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

Edward I. Balmond, David Benito-Alifonso, Diane M. Coe, Roger W. Alder, Eoghan M. McGarrigle, M. Carmen Galan

Research output: Contribution to journalArticle (Academic Journal)peer-review

70 Citations (Scopus)

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.

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

Structured keywords

  • BCS and TECS CDTs

Keywords

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

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