Glycosylation with 2′-thio-S-acetyl participation

Spencer Knapp, Brian A. Kirk

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

Abstract

The reaction of 1,2,3,4,6-penta-O,S,O,O,O-acetyl-2-thio-β -D-glucopyranose with glycosyl acceptors in the presence of trimethylsilyl triflate leads to the β-disaccharides exclusively, owing to especially avid anchimeric assistance by the 2-thio-S-acetyl group. Optional reductive removal of -SAc with Ra-Ni gives the corresponding 2′-deoxy-β -disaccharides.

Original languageEnglish (US)
Pages (from-to)7601-7605
Number of pages5
JournalTetrahedron Letters
Volume44
Issue number41
DOIs
StatePublished - Oct 6 2003

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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