Stannylene‐Mediated Regioselective 6‐O‐Glycosylation of Unprotected Phenyl 1‐Thioglycopyranosides

Agnese Maggi, Robert Madsen

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

A straightforward procedure is described for the synthesis of (1→6)‐linked saccharides by regioselective glycosylation of unprotected glycosyl acceptors. Phenyl 1‐thioglycopyranosides derived from D‐glucose, D‐galactose and D‐mannose were treated with dibutyltin oxide to introduce a stannylene acetal, and then subjected to selective glycosylation at the 6‐position with the Koenigs–Knorr protocol. Peracylated glycosyl bromides of D‐glucose, D‐galactose, D‐mannose and D‐glucosamine were employed as the donors to give the corresponding (1→6)‐linked disaccharides in moderate to good yields. The best results were obtained with glycosyl donors and acceptors derived from D‐glucose and D‐galactose. Fully acylated disaccharide thioglycosides could also serve as glycosyl donors for the regioselective coupling. Brominolysis and subsequent Koenigs–Knorr coupling with the stannylene acetal of phenyl 1‐thio‐β‐D‐glucopyranoside gave rise to the corresponding (1→6)‐linked trisaccharides in moderate yields.
Original languageEnglish
JournalEuropean Journal of Organic Chemistry
Volume2013
Issue number13
Pages (from-to)2683-2691
ISSN1434-193X
DOIs
Publication statusPublished - 2013

Keywords

  • Carbohydrates
  • Glycosylation
  • Protecting groups
  • Regioselectivity
  • Stannanes

Fingerprint

Dive into the research topics of 'Stannylene‐Mediated Regioselective 6‐O‐Glycosylation of Unprotected Phenyl 1‐Thioglycopyranosides'. Together they form a unique fingerprint.

Cite this