Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 8, Issue 1, Pages 171-180Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b915450g
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Funding
- Alberta Ingenuity
- Natural Sciences and Engineering Research Council of Canada (NSERC)
- University of Calgary
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Diisobutylaluminium hydride (DIBAL-H) mediated reductive removal of benzyl groups was investigated for perbenzylated alpha-, beta- and gamma-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 alpha-cyclodextrin, the removal of the third and fourth benzyl groups took a different path involving the secondary rim, compared to beta- and gamma-cyclodextrins which both gave only 6-O-debenzylated products.
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