Stereoselective synthesis of O-serinyl/threoninyl-2-acetamido-2-deoxy-α- or β-glycosides

Lajos Szabó, Jan Ramza, Courtney Langdon, Robin Polt

Research output: Contribution to journalArticle

30 Scopus citations

Abstract

General glycosidation methodology has been developed which can selectively provide 2-acetamido-2-deoxy-α- or β-glycosides of β-hydroxy-α-amino acid derivatives [glucopyranoside-(8, 43), galactopyranoside- (9, 13), mannopyranoside- (10), lactoside analogs (11, 38) and 3-O-β-galactopyranosyl-mannopyranoside (12)] stereoselectively in excellent yield from the highly nucleophilic α-imino esters (Schiff bases) of l-serine and l-threonine. Various glycosides were converted via their amino and acetamido derivatives to Fmoc-protected serinyl- or threoninyl-glycosides (24-28, 37, 41, 46) which are all suitable building blocks for the solid-phase synthesis of O-glycopeptides. Complete 1H- and 13C-NMR data are provided for all compounds.

Original languageEnglish (US)
Pages (from-to)11-28
Number of pages18
JournalCarbohydrate Research
Volume274
Issue numberC
DOIs
StatePublished - Sep 8 1995

Keywords

  • 2-Acetamido-2-deoxy-glycosides
  • Stereoselective synthesis

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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