Issue 1, 1988
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Synthesis of (L)-daunosamine and related amino sugars

Peter G. Sammes  and  Dean Thetford  

Abstract

1-(2-Furyl)ethanol (6) has been converted into methyl (±)-daunosaminide (1) and methyl (±)-ristosaminide (3) by use of an intramolecular cyclisation of a trichloroacetimidate group. (±)-Daunosamine (1) has been obtained more directly from the alcohol (10) by use of a modified Mitsunobu reaction; the scope of the latter reaction has been explored using cyclohex-2-en-1-ol as a model substrate.

Asymmetric reduction of 2-acetylfuran (5) has given (S)-1-(2-furyl)ethanol (46) in good enantiomeric excess, thus providing a short route to the L-enantiomers of the amino sugars (1), (2), and (3) from a cheap, non-carbohydrate precursor.

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Article information

DOI
https://doi.org/10.1039/P19880000111
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1988, 111-123

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Synthesis of (L)-daunosamine and related amino sugars

P. G. Sammes and D. Thetford, J. Chem. Soc., Perkin Trans. 1, 1988, 111 DOI: 10.1039/P19880000111

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