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A 3,4-trans-fused cyclic protecting group facilitates α-selective catalytic synthesis of 2-deoxyglycosides

Research output: Contribution to journalArticle

Original languageEnglish
Pages (from-to)8190-8194
Number of pages5
JournalAngewandte Chemie - International Edition
Volume53
Issue number31
DOIs
DatePublished - 28 Jul 2014

Abstract

A practical approach has been developed to convert glucals and rhamnals into disaccharides or glycoconjugates with high α-selectivity and yields (77-97 %) using a trans-fused cyclic 3,4-O-disiloxane protecting group and TsOH·H2O (1 mol %) as a catalyst. Control of the anomeric selectivity arises from conformational locking of the intermediate oxacarbenium cation. Glucals outperform rhamnals because the C6 side-chain conformation augments the selectivity.

    Research areas

  • conformation analysis, glycosides, homogeneous catalysis, protecting groups, synthetic methods

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