Application of 2-azido-2-deoxythioglycosides for β-glycoside formation and oligosaccharide synthesis

Kwok-Kong Mong*, Yu Fang Yen, Wei Cheng Hung, Yen Hsun Lai, Jiun Han Chen

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

Most natural 2-acetamido-2-deoxyglycosides exist in a 1,2-trans-β- glycosidic configuration. This study investigated the use of 2-azido-2-deoxythioglycosides for 1,2-trans-β-glycosidic bond formation under low-concentration glycosylation conditions. Further application of the 2-azido-2-deoxythioglycosyl substrates for one-pot oligosaccharide synthesis was demonstrated in the synthesis of protected β-(1→6)-N- acetylglucosamine trimer, core-6-serine conjugate, and F1-α serine conjugate.

Original languageEnglish
Pages (from-to)3009-3017
Number of pages9
JournalEuropean Journal of Organic Chemistry
Issue number15
DOIs
StatePublished - 1 May 2012

Keywords

  • Azides
  • Carbohydrates
  • Glycopeptides
  • Glycosylation
  • Regioselectivity

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