Cascade in Situ Phosphorylation and One-Pot Glycosylation for Rapid Synthesis of Heptose-Containing Oligosaccharides

Kwok-Kong Mong*, Kuang Chun Cheng, I. Chen Lu, Chia Wei Pan, Yi Fang Wang, Li Ching Shen

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

We report a one-pot glycosylation strategy for achieving rapid syntheses of heptose (Hep)-containing oligosaccharides. The reported procedure was designed to incorporate an in situ phosphorylation step into an orthogonal one-pot glycosylation. Hep-containing oligosaccharides were assembled directly from building blocks with minimal effort expended on manipulation of protecting and aglycone leaving groups. The utility of our one-pot procedure was illustrated by synthesizing partial core oligosaccharide structure present in the lipopolysaccharide of Ralstonia solanacearum.

Original languageEnglish
Pages (from-to)16060-16071
Number of pages12
JournalJournal of Organic Chemistry
Volume85
Issue number24
DOIs
StatePublished - 18 Dec 2020

Keywords

  • INNER-CORE OLIGOSACCHARIDES
  • CONVERGENT SYNTHESIS
  • LIPOPOLYSACCHARIDE
  • STRATEGY
  • TETRASACCHARIDE
  • DONORS
  • TRISACCHARIDE
  • GLYCOSIDES
  • REACTIVITY
  • CANDIDATE

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