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{"sheet":"general","index":0,"n_rows":25,"n_cols":14,"rows_kept":25,"cut":false,"hidden":false,"merged":[[17,5,17,8]],"flags":["formulas_cached_only"]}
["Environmental assessment of asymmetric syntheses of tembamide"]
[]
["General remarks:"]
["The E-factor was calculated for non-volatiles only, while solvents were treated separately. However, gases and volatile compounds constituting coupled products were included in the E-factor calculation."]
["If no information on conversion was available, reactions were treated as giving complete conversion, and all losses in yield were accounted for as 'unknown by-products'."]
["For hydrogenations, 5-fold excess of hydrogen is assumed."]
["If no information on the amounts of auxiliary materials employed was available, the following values were assumed:"]
[null,"Solvents for diluting solutions: 3 times the initial volume"]
[null,"Celite for filtering solutions: 0.1 g/mL of solution"]
[null,"solvents for extraction: 50 mL/g of crude product"]
[null,"aqueous solutions for washing extracts: 20% of extract volume; brine: 10% of extract volume"]
[null,"anhydrous salts for drying extracts: 0.02 g/mL extract volume"]
[null,"solvents for recrystallisation: 10 mL/g crude product"]
[null,"silica gel for chromatography: 20 g/g of crude product"]
[null,"eluents for chromatography: 500 mL/g of crude product (total eluent volume)"]
["All estimated quantities are typeset in blue."]
[]
[{"$nulls":5},"E-factor",{"$nulls":4},"Waste classification"]
["Article","Starting material","Steps","Asymmetric key step","Overall yield [%]","overall","reaction","isolation","purification","Solvent demand [mL/g]","Inorg. salts","Organics","silica gel","others"]
["Present work","2-bromo-4'-methoxyacetophenone","4 (1)","asymmetric ketone reduction (ADH)",73,11.1,3.2,7.8,"na",309,9.6,1.1,"na",0.3]
["Lee et al. 2007","4'-methoxyacetophenone","5 (5)","asymmetric ketone reduction (Rh catalyst)",62,57.8,4.4,5.2,48.2,1600,5.8,4.2,47.3,1.2]
["Baeza et al. 2005","4-methoxybenzaldehyde","3 (2)","asymmetric cyano-O-phosphorylation (Lewis acid/Brønsted base catalyst)",65,23.3,5.8,17.6,"na",1031,19.5,3.7,"na",0.1]
["Kamal et al. 2004","2-azido-4'-methoxyacetophenone","5 (4)","enantioselective transesterification (lipase)",42,114.9,19.7,38.7,56.5,1801,39.3,6.4,56.1,12.2]
["Yadav et al. 2001","2-azido-4'-methoxyacetophenone","3 (2)","asymmetric ketone reduction (carrot root)",85,97.5,77.8,4.3,15.4,826,4.8,0.1,15.4,77.2]
["Brown et al. 1993, 1994","4-methoxybenzaldehyde","3 (3)","asymmetric hydrocyanation (peptide catalyst)",72,14.6,5.2,9.4,"na",483,13.7,0.5,"na",0.4]

{"sheet":"4-step, 1-pot","index":1,"n_rows":43,"n_cols":9,"rows_kept":43,"cut":false,"hidden":false,"merged":[[0,0,0,8]],"flags":["formulas_cached_only"]}
["Chemo-enzymatic 4-step, 1-pot sequence"]
["present study"]
[]
["(S)-tembamide"]
["overall yield:",0.73]
["ee (HPLC):",">99%"]
[]
["Step 1:","(S)-tembamide"]
["yield [g]:",0.984]
["yield [%]:",0.73]
[]
["Material","Non-volatile [g]","Non-volatile [E]","Solvent [mL]","Solvent [mL/g]",null,null,"E factor:"]
["Starting Materials",{"$nulls":6},"reaction",3.2175]
["substrate 1e",1.145,{"$nulls":5},"work-up",7.8468]
["NaN3",0.39,0.0663,{"$nulls":4},"purification","na"]
["KI",0.083,0.0847,{"$nulls":4},"total",11.0643]
["2-PrOH",null,null,5,5.08130081300813]
["NAD+",0.0033,0.0034,{"$nulls":4},"solvent demand:","[mL/g]"]
["KRED-NADH-110",0.025,0.0255,{"$nulls":4},"water",116.0569105691057]
["H2",0.091,0.0823,{"$nulls":4},"EtOAc",111.78861788617887]
["Pd-NPs",0.047,0.048,4.5,4.573170731707317,null,null,"MTBE",15.24390243902439]
["BzCl",0.843,0.1434,{"$nulls":4},"2-PrOH",5.08130081300813]
["phosphate buffer",0.77,0.8684,52.5,53.353658536585364,null,null,"EtOH",60.97560975609756]
["4 M aq. NaOH",0.352,0.1551,2.2,2.2357723577235773,null,null,"total",309.1463414634147]
["MTBE",null,null,15,15.24390243902439]
[]
["By-Products"]
["NaBr",null,0.3792]
["acetone",null,0.2141]
["nitrogen",null,0.1033]
["NaCl",null,0.2154]
["water",null,0.0664]
["unknown by-products",null,0.762]
[]
["Auxiliaries (Work-Up)"]
["EtOAc",null,null,110,111.78861788617887]
["1 M aq. NaOH",1.6,1.6325,40,40.65040650406504]
["brine",3.59,3.6633,10,10.16260162601626]
["MgSO4",2.5,2.551]
[]
["Auxiliaries (Purification)"]
["EtOH",null,null,60,60.97560975609756]
["water",null,null,15,15.24390243902439]

{"sheet":"Lee et al. 2007","index":2,"n_rows":122,"n_cols":12,"rows_kept":122,"cut":false,"hidden":false,"merged":[[0,0,0,8]],"flags":["formulas_cached_only"]}
["Asymmetric transfer hydrogenation of 2-tosyloxy-1-(4-hydroxyphenyl)ethanone derivatives"]
["D.-M. Lee, J.-C. Lee, N. Jeong, K.-I. Lee, Tetrahedron: Asymmetry 2007, 18, 2662–2667."]
[]
["(R)-tembamide"]
["overall yield:",0.62195588]
["ee:",">99%"]
[]
["Step 1:","1-(4-methoxyphenyl)-2-(p-tolylsulfonyloxy)ethanone (6a)"]
["yield [g]:",3.56]
["yield [%]:",0.85]
[]
["Material","Non-volatile [g]","Non-volatile [E]","Solvent [mL]","Solvent [mL/g]",null,null,"E factor:"]
["Starting Materials",{"$nulls":6},"reaction",0.398]
["substrate",0.9,{"$nulls":5},"work-up","na"]
["HTIB",3,0.398,{"$nulls":4},"purification",0.9918]
["MeCN",null,null,60,16.853932584269664,null,null,"total",1.3898000000000001]
[]
["By-Products",{"$nulls":6},"solvent demand:","[mL/g]"]
["PhI",null,0.6368,{"$nulls":4},"MeCN",16.8]
["water",null,0.0562,{"$nulls":4},"EtOH",8.4]
["unknown by-products",null,0.2988,{"$nulls":4},"total",25.200000000000003]
[]
["Auxiliaries (Purification)"]
["EtOH",null,null,30,8.426966292134832]
[]
[]
["Step 2:","(R)-1-(4-methoxyphenyl)-2-(p-tolylsulfonyloxy)ethanol (7a)"]
["yield [g]:",1.48]
["yield [%]:",0.92]
[]
["Material","Non-volatile [g]","Non-volatile [E]","Solvent [mL]","Solvent [mL/g]",null,null,"E factor:",null,null,"cumulative E factor:"]
["Starting Materials",{"$nulls":6},"reaction",0.6735899999999999,null,"reaction",1.1038602702702702]
["substrate 6a",1.6,{"$nulls":5},"work-up",0.7432,null,"work-up",0.7432]
["formic acid",0.871,0.4331,{"$nulls":4},"purification",20.2703,null,"purification",21.342516216216215]
["triethylamine",null,null,0.286,0.19324324324324324,null,null,"total",21.687089999999998,null,"total",23.189576486486484]
["Rh-catalyst",0.00398,0.00269]
["EtOAc",null,null,35,23.64864864864865,null,null,"solvent demand:","[mL/g]",null,"cumulative solvent demand:","[mL/g]"]
[{"$nulls":7},"EtOAc",47.770270270270274,null,"MeCN",18.162162162162165]
["By-Products",{"$nulls":6},"CHCl3",482.6351351351351,null,"EtOH",9.081081081081082]
["CO2",null,0.1365,{"$nulls":4},"water",7.4324324324324325,null,"EtOAc",47.770270270270274]
["unknown by-products",null,0.1013,{"$nulls":4},"triethylamine",0.19324324324324324,null,"CHCl3",482.6351351351351]
[{"$nulls":7},"total",538.0310810810811,null,"water",7.4324324324324325]
["Auxiliaries (Work-Up)",{"$nulls":9},"triethylamine",0.19324324324324324]
["EtOAc",null,null,20,13.513513513513514,{"$nulls":5},"total",565.2743243243243]
["water",null,null,11,7.4324324324324325]
["Na2SO4",1.1,0.7432]
[]
["Auxiliaries (Purification)"]
["EtOAc",null,null,35.7,24.121621621621625]
["CHCl3",null,null,714.3,482.6351351351351]
["silica gel",30,20.2703]
[]
[]
["Step 3:","(R)-2-azido-1-(p-methoxyphenyl)ethanol (8)"]
["yield [g]:",0.95]
["yield [%]:",0.91]
[]
["Material","Non-volatile [g]","Non-volatile [E]","Solvent [mL]","Solvent [mL/g]",null,null,"E factor:",null,null,"cumulative E factor:"]
["Starting Materials",{"$nulls":6},"reaction",1.5579,null,"reaction",3.568087650071124]
["substrate 7a",1.73,{"$nulls":5},"work-up",0.6316,null,"work-up",1.985006315789474]
["NaN3",0.7,0.3641,{"$nulls":4},"purification",21.0526,null,"purification",59.918445320056904]
["DMSO",null,null,12,12.631578947368421,null,null,"total",23.2421,null,"total",65.4715392859175]
[]
["By-Products",{"$nulls":6},"solvent demand:","[mL/g]",null,"cumulative solvent demand:","[mL/g]"]
["NaOTs",null,1.005,{"$nulls":4},"EtOAc",97.36842105263159,null,"MeCN",33.074253200569]
["unknown by-products",null,0.1888,{"$nulls":4},"hexanes",460.5263157894737,null,"EtOH",16.5371266002845]
[{"$nulls":7},"water",15.789473684210527,null,"EtOAc",184.36059743954482]
["Auxiliaries (Work-Up)",{"$nulls":6},"DMSO",12.631578947368421,null,"CHCl3",878.9039829302986]
["water",null,null,15,15.789473684210527,null,null,"total",586.3157894736843,null,"water",29.324324324324326]
["EtOAc",null,null,30,31.578947368421055,{"$nulls":5},"triethylamine",0.3519061166429588]
["Na2SO4",0.6,0.6316,{"$nulls":7},"hexanes",460.5263157894737]
[{"$nulls":10},"DMSO",12.631578947368421]
["Auxiliaries (Purification)",{"$nulls":9},"total",1615.7100853485065]
["EtOAc",null,null,62.5,65.78947368421053]
["hexane",null,null,437.5,460.5263157894737]
["silica gel",20,21.0526]
[]
[]
["Step 4:","(R)-2-amino-1-(p-methoxyphenyl)ethanol (9)"]
["yield [g]:",0.59]
["yield [%]:",0.95]
[]
["Material","Non-volatile [g]","Non-volatile [E]","Solvent [mL]","Solvent [mL/g]",null,null,"E factor:",null,null,"cumulative E factor:"]
["Starting Materials",{"$nulls":6},"reaction",0.3018,null,"reaction",4.595600392458471]
["substrate 8",0.71,{"$nulls":5},"work-up",1.0169,null,"work-up",3.405636413916146]
["hydrogen",0.03709,0.0503,{"$nulls":4},"purification","na",null,"purification",72.10524775803458]
["Pd/C",0.02,0.0339,{"$nulls":4},"total",1.3187,null,"total",80.1064845644092]
["MeOH",null,null,6,10.16949152542373]
[{"$nulls":7},"solvent demand:","[mL/g]",null,"cumulative solvent demand:","[mL/g]"]
["By-Products",{"$nulls":6},"MeOH",10.16949152542373,null,"MeCN",39.8012199532271]
["nitrogen",null,0.1675,{"$nulls":4},"total",10.16949152542373,null,"EtOH",19.90060997661355]
["unknown by-products",null,0.0501,{"$nulls":7},"EtOAc",221.85766810521494]
[{"$nulls":10},"CHCl3",1057.6641150517153]
["Auxiliaries (Work-Up)",{"$nulls":9},"water",35.28859367842419]
["Celite",0.6,1.0169,{"$nulls":7},"triethylamine",0.4234802420618657]
[{"$nulls":10},"hexanes",554.192685102587]
[{"$nulls":10},"DMSO",15.2007136485281]
["Step 5:","(R)-tembamide",{"$nulls":8},"MeOH",10.16949152542373]
["yield [g]:",0.2496,{"$nulls":8},"total",1672.9390792487402]
["yield [%]:",0.92]
[]
["Material","Non-volatile [g]","Non-volatile [E]","Solvent [mL]","Solvent [mL/g]",null,null,"E factor:",null,null,"cumulative E factor:"]
["Starting Materials",{"$nulls":6},"reaction",1.3072,null,"reaction",4.38198071130034]
["substrate 9",0.167,{"$nulls":5},"work-up",2.8765,null,"work-up",5.155110901939088]
["BzCl",0.169,0.1126,{"$nulls":4},"purification","na",null,"purification",48.24349509451833]
["aq. NaOH",0.24,0.8013,3,12.01923076923077,null,null,"total",4.1837,null,"total",57.78058670775776]
["toluene",null,null,1,4.006410256410256]
["CH2Cl2",null,null,3,12.01923076923077,null,null,"solvent demand:","[mL/g]",null,"cumulative solvent demand:","[mL/g]"]
[{"$nulls":7},"CH2Cl2",72.11538461538461,null,"MeCN",26.629822644987684]
["By-Products",{"$nulls":6},"EtOH",96.15384615384616,null,"EtOH",109.46875747634]
["NaCl",null,0.2154,{"$nulls":4},"water",120.19230769230771,null,"EtOAc",148.4384237723193]
["water",null,0.0664,{"$nulls":4},"toluene",4.006410256410256,null,"CHCl3",707.6518718495051]
["unknown by-products",null,0.1115,{"$nulls":4},"total",292.46794871794873,null,"water",143.80286516144568]
[{"$nulls":10},"triethylamine",0.28333814272568736]
["Auxiliaries (Work-Up)",{"$nulls":9},"hexanes",370.79398402296493]
["water",null,null,21,84.13461538461539,{"$nulls":5},"DMSO",10.170349276058465]
["CH2Cl2",null,null,15,60.09615384615385,{"$nulls":5},"MeOH",6.804106910039115]
["brine",0.718,2.8765,2,8.012820512820513,{"$nulls":5},"CH2Cl2",72.11538461538461]
[{"$nulls":10},"toluene",4.006410256410256]
["Auxiliaries (Purification)",{"$nulls":9},"total",1600.1653141281806]
["EtOH",null,null,24,96.15384615384616]
["water",null,null,6,24.03846153846154]

{"sheet":"Baeza et al. 2005","index":3,"n_rows":57,"n_cols":12,"rows_kept":57,"cut":false,"hidden":false,"merged":[[0,0,0,8]],"flags":["formulas_cached_only"]}
["Synthesis of Enantioenriched Cyanohydrin O-Phosphates"]
["A. Baeza, C. Nájera, J. M. Sansano, J. M. Saá, Chem. Eur. J. 2005, 11, 3849–3862."]
[]
["(S)-tembamide"]
["overall yield:",0.6525]
["ee:",0.98]
[]
["Step 1:","(R)-2-(diethylphosphoryloxy)-2-(4-methoxyphenyl)acetonitrile (3c)"]
["yield [g]:",0.0651]
["yield [%]:",0.87]
[]
["Material","Non-volatile [g]","Non-volatile [E]","Solvent [mL]","Solvent [mL/g]",null,null,"E factor:"]
["Starting Materials",{"$nulls":6},"reaction",1.444]
["substrate",0.034,{"$nulls":5},"work-up",10.5854]
["diethyl cyanophosphonate",0.1223,1.253,{"$nulls":4},"purification","na"]
["Me2AlCl",0.0023,0.0355,0.025,0.38402457757296465,null,null,"total",12.029399999999999]
["BINOLAM ligand 2",0.0114,0.0061]
["toluene",null,null,1,15.360983102918585,null,null,"solvent demand:","[mL/g]"]
[{"$nulls":7},"toluene",15.360983102918585]
["By-Products",{"$nulls":6},"hexanes",0.38402457757296465]
["unknown by-products",null,0.1494,{"$nulls":4},"water",107.52688172043011]
[{"$nulls":7},"EtOAc",337.9416282642089]
["Auxiliaries (Work-Up)",{"$nulls":6},"total",123.27188940092167]
["2 M aq. HCl",0.0729,1.1215,2,30.72196620583717]
["EtOAc",null,null,22,337.9416282642089]
["NH4Cl buffer",0.176,2.704,5,76.80491551459293]
["MgSO4",0.44,6.7599]
[]
[]
["Step 2:","(R)-tembamide"]
["yield [g]:",0.0509]
["yield [%]:",0.75]
[]
["Material","Non-volatile [g]","Non-volatile [E]","Solvent [mL]","Solvent [mL/g]",null,null,"E factor:",null,null,"cumulative E factor:"]
["Starting Materials",{"$nulls":6},"reaction",3.6334999999999997,null,"reaction",5.761201375245579]
["substrate 3c",0.075,{"$nulls":5},"work-up",1.9657,null,"work-up",17.563047740667976]
["LiAlH4",0.049,0.5596,{"$nulls":4},"purification","na",null,"purification","na"]
["1 M aq. NaOH",0.015,0.0983,0.375,7.367387033398821,null,null,"total",5.5992,null,"total",23.324249115913556]
["BzCl",0.0534,0.3592]
["THF",null,null,7,137.52455795677798,null,null,"solvent demand:","[mL/g]",null,"cumulative solvent demand:","[mL/g]"]
[{"$nulls":7},"THF",137.52455795677798,null,"toluene",22.634061546540156]
["By-Products",{"$nulls":6},"water",105.59921414538312,null,"hexanes",10.38903424986193]
["Al(OH)3",null,0.575,{"$nulls":4},"EtOAc",98.23182711198429,null,"water",264.03764497116424]
["H3PO4",null,0.3612,{"$nulls":4},"n-hexane",9.823182711198427,null,"EtOAc",596.1811811358677]
["LiOH",null,0.1765,{"$nulls":4},"total",341.3555992141454,null,"THF",137.52455795677798]
["H2",null,0.0446,{"$nulls":7},"total",1030.766479860212]
["NaCl",null,0.2154]
["EtOH",null,0.3396]
["unknown by-products",null,0.9041]
[]
["Auxiliaries (Work-Up)"]
["water",null,null,5,98.23182711198429]
["EtOAc",null,null,5,98.23182711198429]
["MgSO4",0.1,1.9657]
[]
["Auxiliaries (Purification)"]
["n-hexane",null,null,0.5,9.823182711198427]

{"sheet":"Kamal et al. 2004","index":4,"n_rows":96,"n_cols":12,"rows_kept":96,"cut":false,"hidden":false,"merged":[[0,0,0,8]],"flags":["formulas_cached_only"]}
["Chemoenzymatic synthesis of (R)- and (S)-tembamide by a one-pot lipase resolution protocol"]
["A. Kamal, A. A. Shaik, M. Sandbhor, M. S. Malik, Tetrahedron: Asymmetry 2004, 15, 3939–3944."]
[]
["(S)-tembamide"]
["overall yield:",0.422037]
["ee:",">99%"]
[]
["Step 1:","(S)-2-azido-1-(4-methoxyphenyl)-1-ethyl acetate (6a)"]
["yield [g]:",0.115]
["yield [%]:",0.49]
[]
["Material","Non-volatile [g]","Non-volatile [E]","Solvent [mL]","Solvent [mL/g]",null,null,"E factor:"]
["Starting Materials",{"$nulls":6},"reaction",16.1937]
["substrate",0.191,{"$nulls":5},"work-up",32.8798]
["NaBH4",0.076,0.3282,{"$nulls":4},"purification",34.7016]
["activated alumina",1,8.6754,{"$nulls":4},"total",83.77510000000001]
["lipase PS-C",0.191,1.657]
["isopropenyl acetate",0.601,4.777,{"$nulls":4},"solvent demand:","[mL/g]"]
["DIPE",null,null,10,86.95652173913044,null,null,"DIPE",86.95652173913044]
[{"$nulls":7},"water",26.08695652173913]
["By-Products",{"$nulls":6},"hexanes/EtOAc",869.5652173913043]
["borane",null,0.1176,{"$nulls":4},"total",982.6086956521738]
["NaOH",null,0.3401]
["acetone",null,0.2469]
["unknown by-products",null,0.0515]
[]
["Auxiliaries (Work-Up)"]
["water",null,null,2,17.391304347826086]
["brine",3.59,31.1447,1,8.695652173913043]
["Na2SO4",0.2,1.7351]
[]
["Auxiliaries (Purification)"]
["silica gel",4,34.7016]
["hexanes/EtOAc",null,null,100,869.5652173913043]
[]
[]
["Step 2:","(S)-2-azido-1-(4-methoxyphenyl)-1-ethanol (5a)"]
["yield [g]:",0.0944]
["yield [%]:",1]
[]
["Material","Non-volatile [g]","Non-volatile [E]","Solvent [mL]","Solvent [mL/g]",null,null,"E factor:",null,null,"cumulative E factor:"]
["Starting Materials",{"$nulls":6},"reaction",2.5009,null,"reaction",22.22839470338983]
["substrate 6a",0.115,{"$nulls":5},"work-up","na",null,"work-up",40.05484110169492]
["K2CO3",0.2,2.1175,{"$nulls":4},"purification","na",null,"purification",42.274194915254235]
["MeOH",null,null,5,52.96610169491525,null,null,"total",2.5009,null,"total",104.55743072033898]
[]
["By-Products",{"$nulls":6},"solvent demand:","[mL/g]",null,"cumulative solvent demand:","[mL/g]"]
["methyl acetate",null,0.3834,{"$nulls":4},"MeOH",52.96610169491525,null,"DIPE",105.9322033898305]
[{"$nulls":7},"EtOAc",105.9322033898305,null,"water",31.779661016949152]
["Auxiliaries (Work-Up)",{"$nulls":6},"total",158.89830508474574,null,"hexanes/EtOAc",1059.322033898305]
["EtOAc",null,null,10,105.9322033898305,{"$nulls":5},"MeOH",52.96610169491525]
[{"$nulls":10},"EtOAc",105.9322033898305]
[{"$nulls":10},"total",1355.9322033898304]
["Step 3:","(S)-2-amino-1-(4-methoxyphenyl)-1-ethanol (7)"]
["yield [g]:",0.497]
["yield [%]:",0.99]
[]
["Material","Non-volatile [g]","Non-volatile [E]","Solvent [mL]","Solvent [mL/g]",null,null,"E factor:",null,null,"cumulative E factor:"]
["Starting Materials",{"$nulls":6},"reaction",0.3286,null,"reaction",26.224456203747913]
["substrate 5a",0.579,{"$nulls":5},"work-up",2.0137,null,"work-up",48.67718691726631]
["hydrogen",0.0302,0.0487,{"$nulls":4},"purification","na",null,"purification",49.24901178255976]
["Pd/C",0.05,0.1007,{"$nulls":4},"total",2.3423,null,"total",124.15065490357398]
["MeOH",null,null,10,20.120724346076457]
[{"$nulls":7},"solvent demand:","[mL/g]",null,"cumulative solvent demand:","[mL/g]"]
["By-Products",{"$nulls":6},"MeOH",20.120724346076457,null,"DIPE",123.40995123282065]
["nitrogen",null,0.1675,{"$nulls":4},"total",20.120724346076457,null,"water",37.02298536984619]
["unknown by-products",null,0.0117,{"$nulls":7},"hexanes/EtOAc",1234.0995123282064]
[{"$nulls":10},"MeOH",81.82569996248678]
["Auxiliaries (Work-Up)",{"$nulls":9},"EtOAc",123.40995123282065]
["Celite",1,2.0137,{"$nulls":7},"total",1599.7681001261808]
[]
[]
["Step 4:","(S)-tembamide"]
["yield [g]:",0.7]
["yield [%]:",0.87]
[]
["Material","Non-volatile [g]","Non-volatile [E]","Solvent [mL]","Solvent [mL/g]",null,null,"E factor:",null,null,"cumulative E factor:"]
["Starting Materials",{"$nulls":6},"reaction",0.9351,null,"reaction",19.7417814489735]
["substrate 7",0.502,{"$nulls":5},"work-up",3.7493,null,"work-up",38.65779690352527]
["Et3N",0.42,0.1429,{"$nulls":4},"purification",21.1825,null,"purification",56.50107702120715]
["BzCl",0.464,0.0596,{"$nulls":4},"total",25.8669,null,"total",114.90065537370593]
["CH2Cl2",null,null,10,14.285714285714286]
[{"$nulls":7},"solvent demand:","[mL/g]",null,"cumulative solvent demand:","[mL/g]"]
["By-Products",{"$nulls":6},"CH2Cl2",67.85714285714286,null,"DIPE",88.50256502696567]
["Et3N·HCl",null,0.5074,{"$nulls":4},"water",49.642857142857146,null,"water",76.19362665094684]
["unknown by-products",null,0.2252,{"$nulls":4},"hexanes/EtOAc",535.7142857142858,null,"hexanes/EtOAc",1420.7399359839424]
[{"$nulls":7},"total",653.2142857142858,null,"MeOH",58.68071625881195]
["Auxiliaries (Work-Up)",{"$nulls":9},"EtOAc",88.50256502696567]
["water",null,null,30,42.85714285714286,{"$nulls":5},"CH2Cl2",67.85714285714286]
["CH2Cl2",null,null,37.5,53.57142857142858,{"$nulls":5},"total",1800.4765518047755]
["brine",1.705,2.4077,4.75,6.7857142857142865]
["Na2SO4",0.95,1.3416]
[]
["Auxiliaries (Purification)"]
["silica gel",15,21.1825]
["hexanes/EtOAc",null,null,375,535.7142857142858]

{"sheet":"Yadav et al. 2001","index":5,"n_rows":59,"n_cols":12,"rows_kept":59,"cut":false,"hidden":false,"merged":[[0,0,0,8]],"flags":["formulas_cached_only"]}
["Stereoselective synthesis of (R)-tembamide via asymmetric reduction of azidoketones by Daucus carota"]
["J. S. Yadav, P. T. Reddy, S. Nanda, A. B. Rao, Tetrahedron: Asymmetry 2001, 12, 3381–3385."]
[]
["(R)-tembamide"]
["overall yield:",0.8464]
["ee:",">99%"]
[]
["Step 1:","(R)-2-azido-1-(4-methoxyphenyl)ethanol (5a)"]
["yield [g]:",0.929]
["yield [%]:",0.92]
[]
["Material","Non-volatile [g]","Non-volatile [E]","Solvent [mL]","Solvent [mL/g]",null,null,"E factor:"]
["Starting Materials",{"$nulls":6},"reaction",107.6486]
["substrate",1,{"$nulls":5},"work-up",6.0127]
["carrot root",100,107.5616,{"$nulls":4},"purification",21.5123]
["EtOH",null,null,1.5,1.6146393972012916,null,null,"total",135.1736]
["water",null,null,400,430.57050592034443]
[{"$nulls":7},"solvent demand:","[mL/g]"]
["By-Products",{"$nulls":6},"water",441.33476856835307]
["unknown by-products",null,0.087,{"$nulls":4},"EtOH",1.6146393972012916]
[{"$nulls":7},"diethyl ether",107.64262648008611]
["Auxiliaries (Work-Up)",{"$nulls":6},"n-hexane",511.302475780409]
["diethyl ether",null,null,100,107.64262648008611,null,null,"EtOAc",26.910656620021527]
["brine",3.59,3.8615,10,10.76426264800861,null,null,"total",1088.805166846071]
["Na2SO4",2,2.1512]
[]
["Auxiliaries (Purification)"]
["silica gel",20,21.5123]
["n-hexane",null,null,475,511.302475780409]
["EtOAc",null,null,25,26.910656620021527]
[]
[]
["Step 2:","(R)-tembamide"]
["yield [g]:",1.08]
["yield [%]:",0.92]
[]
["Material","Non-volatile [g]","Non-volatile [E]","Solvent [mL]","Solvent [mL/g]",null,null,"E factor:",null,null,"cumulative E factor:"]
["Starting Materials",{"$nulls":6},"reaction",0.8667000000000001,null,"reaction",77.81551407407407]
["substrate 5a",0.772,{"$nulls":5},"work-up","na",null,"work-up",4.297967037037036]
["hydrogen",0.0403,0.0299,{"$nulls":4},"purification","na",null,"purification",15.37731074074074]
["Pd/C",0.02,0.0185,{"$nulls":4},"total",0.8667000000000001,null,"total",97.49079185185185]
["MeOH",null,null,5,4.62962962962963]
["50% aq. NaOH",0.48,0.2963,6.5,6.018518518518518,null,null,"solvent demand:","[mL/g]",null,"cumulative solvent demand:","[mL/g]"]
["BzCl",0.703,0.1302,{"$nulls":4},"MeOH",4.62962962962963,null,"water",351.12077901367456]
["CH2Cl2",null,null,5,4.62962962962963,null,null,"CH2Cl2",4.62962962962963,null,"EtOH",8.561575569110552]
["toluene",null,null,3,2.7777777777777777,null,null,"toluene",2.7777777777777777,null,"diethyl ether",76.94454411354303]
[{"$nulls":7},"water",35.648148148148145,null,"n-hexane",365.4865845393294]
["By-Products",{"$nulls":6},"EtOH",7.4074074074074066,null,"EtOAc",19.236136028385758]
["nitrogen",null,0.1033,{"$nulls":4},"total",55.09259259259259,null,"MeOH",4.62962962962963]
["NaCl",null,0.2154,{"$nulls":7},"CH2Cl2",4.62962962962963]
["water",null,0.0664,{"$nulls":7},"toluene",2.7777777777777777]
["unknown by-products",null,0.0067,{"$nulls":7},"total",825.979248893673]
[]
["Auxiliaries (Work-Up)"]
["water",null,null,30,27.777777777777775]
[]
["Auxiliaries (Purification)"]
["EtOH",null,null,8,7.4074074074074066]
["water",null,null,2,1.8518518518518516]

{"sheet":"Brown et al. 1994","index":6,"n_rows":73,"n_cols":12,"rows_kept":73,"cut":false,"hidden":false,"merged":[[0,0,0,8]],"flags":["formulas_cached_only"]}
["Peptide-catalysed enantioselective hydrocyanation of aldehydes"]
["R. F. C. Brown, A. C. Donohue, W. R. Jackson, T. D. McCarthy, Tetrahedron 1994, 50, 13739–13752; R. F. C. Brown, W. R. Jackson, T. D. McCarthy, Tetrahedron: Asymmetry 1993, 4, 205–206."]
[]
["(R)-tembamide"]
["overall yield:",0.7191]
["ee:",">99%"]
[]
["Step 1:","(R)-2-hydroxy-(4-methoxyphenyl)acetonitrile (5)"]
["yield [g]:",2.365]
["yield [%]:",0.94]
[]
["Material","Non-volatile [g]","Non-volatile [E]","Solvent [mL]","Solvent [mL/g]",null,null,"E factor:"]
["Starting Materials",{"$nulls":6},"reaction",0.48429999999999995]
["substrate",2.1,{"$nulls":5},"work-up","na"]
["HCN",1.351,0.3951,{"$nulls":4},"purification","na"]
["peptide catalyst",0.06,0.0254,{"$nulls":4},"total",0.48429999999999995]
["toluene",null,null,8,3.3826638477801265]
[{"$nulls":7},"solvent demand:","[mL/g]"]
["By-Products",{"$nulls":6},"toluene",3.3826638477801265]
["unknown by-products",null,0.0638,{"$nulls":4},"diethyl ether",42.28329809725158]
[{"$nulls":7},"petroleum ether/CH2Cl2",10.570824524312895]
["Auxiliaries (Work-Up)",{"$nulls":6},"total",56.23678646934461]
["diethyl ether",null,null,100,42.28329809725158]
[]
["Auxiliaries (Purification)"]
["petroleum ether/CH2Cl2",null,null,25,10.570824524312895]
[]
[]
["Step 2:","(R)-2-amino-1-(4-methoxyphenyl)ethanol (6)"]
["yield [g]:",0.595]
["yield [%]:",0.85]
[]
["Material","Non-volatile [g]","Non-volatile [E]","Solvent [mL]","Solvent [mL/g]",null,null,"E factor:",null,null,"cumulative E factor:"]
["Starting Materials",{"$nulls":6},"reaction",1.6984,null,"reaction",2.2559554621848736]
["substrate 5",0.685,{"$nulls":5},"work-up",2.4848,null,"work-up",2.4848]
["LiAlH4",0.32,0.0022,{"$nulls":4},"purification","na",null,"purification","na"]
["THF",null,null,20,33.61344537815126,null,null,"total",4.183199999999999,null,"total",4.7407554621848735]
[]
["By-Products",{"$nulls":6},"solvent demand:","[mL/g]",null,"cumulative solvent demand:","[mL/g]"]
["LiOH",null,0.2865,{"$nulls":4},"THF",33.61344537815126,null,"toluene",3.8943272869401464]
["Al(OH)3",null,0.933,{"$nulls":4},"diethyl ether/petroleum ether",11.764705882352942,null,"diethyl ether",48.679091086751825]
["hydrogen",null,0.0723,{"$nulls":4},"total",45.378151260504204,null,"petroleum ether/CH2Cl2",12.169772771687956]
["unknown by-products",null,0.4044,{"$nulls":7},"THF",33.61344537815126]
[{"$nulls":10},"diethyl ether/petroleum ether",11.764705882352942]
["Auxiliaries (Work-Up)",{"$nulls":9},"total",110.12134240588414]
["Na2SO4 · 10 H2O",1.083,1.8144]
["Na2SO4",0.4,0.6704]
[]
["Auxiliaries (Purification)"]
["diethyl ether/petroleum ether",null,null,7,11.764705882352942]
[]
[]
["Step 3:","(R)-tembamide"]
["yield [g]:",0.147]
["yield [%]:",0.9]
[]
["Material","Non-volatile [g]","Non-volatile [E]","Solvent [mL]","Solvent [mL/g]",null,null,"E factor:",null,null,"cumulative E factor:"]
["Starting Materials",{"$nulls":6},"reaction",3.6730999999999994,null,"reaction",5.207763579717601]
["substrate 6",0.1,{"$nulls":5},"work-up",7.7075,null,"work-up",9.397840136054421]
["10% aq. NaOH",0.5,3.2489,{"$nulls":4},"purification","na",null,"purification","na"]
["BzCl",0.084,{"$nulls":5},"total",11.3806,null,"total",14.605603715772023]
["benzene",null,null,10,68.02721088435375]
[{"$nulls":7},"solvent demand:","[mL/g]",null,"cumulative solvent demand:","[mL/g]"]
["By-Products",{"$nulls":6},"benzene",68.02721088435375,null,"toluene",2.6492022360137053]
["NaCl",null,0.2154,{"$nulls":4},"EtOAc",68.02721088435375,null,"diethyl ether",33.11502795017131]
["water",null,0.0664,{"$nulls":4},"water",272.108843537415,null,"petroleum ether/CH2Cl2",8.278756987542828]
["unknown by-products",null,0.1424,{"$nulls":4},"total",408.1632653061225,null,"THF",22.86628937289202]
[{"$nulls":10},"diethyl ether/petroleum ether",8.003201280512206]
["Auxiliaries (Work-Up)",{"$nulls":9},"benzene",68.02721088435375]
["EtOAc",null,null,10,68.02721088435375,{"$nulls":5},"EtOAc",68.02721088435375]
["1 M aq. HCl",0.729,4.9773,20,136.0544217687075,{"$nulls":5},"water",272.108843537415]
["water",null,null,20,136.0544217687075,{"$nulls":5},"total",483.07574313325455]
["MgSO4",0.4,2.7302]