A straightforward α-selective aromatic glycosylation and its application for stereospecific synthesis of 4-methylumbelliferyl α-T-antigen

Shih Sheng Chang, Chun Cheng Lin, Yaw-Kuen Li*, Kwok-Kong Mong

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

A practical and efficient α-selective aromatic glycosylation with simple per-O-acetyl glycopyranosyl trichloroacetimidates is reported. The method is particularly effective for L-fucosyl and 2-azido-2-deoxy-d-galatosaminyl imidates, with which exclusive α-selectivity was achieved. The synthetic utility of this method was demonstrated in the stereoselective synthesis of 4-methylumbelliferyl α-T-antigen.

Original languageEnglish
Pages (from-to)432-438
Number of pages7
JournalCarbohydrate Research
Volume344
Issue number4
DOIs
StatePublished - 10 Mar 2009

Keywords

  • Aromatic
  • Glycosylation
  • Imidate
  • Stereoselective
  • α-T-Antigen

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