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Paper

Org. Biomol. Chem., 2010, 8, 171 - 180, DOI: 10.1039/b915450g

DIBAL-H mediated triple and quadruple debenzylations of perbenzylated cyclodextrins

Girish K. Rawal, Shikha Rani, Sandra Ward and Chang-Chun Ling

Diisobutylaluminium hydride (DIBAL-H) mediated reductive removal of benzyl groups was investigated for perbenzylated -, - and -cyclodextrins using DIBAL-H in hexane as the reagent. It was found that under the new conditions, the debenzylation can be better controlled to provide sequentially tri- and tetra-debenzylated products in moderate yields and in a regioselective manner. In the case of -cyclodextrin, the removal of the third and fourth benzyl groups took a different path involving the secondary rim, compared to - and -cyclodextrins which both gave only 6-O-debenzylated products.

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