(2-Ketulosonyl)onate 2,3-O-thionocarbonate donors for the synthesis of KO and KDO alpha-glycosides and a one-pot glycosylation method for 2-keto acid donors

Kwok-Kong Mong*, Tapan Kumar Pradhan, Cheng-Hsin Chiu, Wei-Cheng Hung, Chao-Ju Chen, Yi-Fang Wang

*Corresponding author for this work

Research output: Contribution to journalArticle

Abstract

We report a short synthetic strategy for direct preparation of (2-ketulosonyl)onate donors. These donors feature a cyclic thionocarbonate group at the C2 and C3 positions, which plays a multitude of chemical roles. It protects the C2 and C3 hydroxyls during building block preparation. In glycosylation, the thionocarbonate can be activated by a sulfenylating promoter and serves as a leaving group. Because of its beta-configuration, it also plays the role of a stereo-directing group during the formation of the alpha-glycosidic bond. In addition, the thionocarbonate donors can couple with thioglycoside acceptors. This orthogonal property was used for the development of the first one-pot glycosylation method for 2-keto acid sugars.

Original languageEnglish
Pages (from-to)2179-2186
Number of pages8
JournalOrganic Chemistry Frontiers
Volume7
Issue number16
DOIs
StatePublished - 21 Aug 2020

Keywords

  • INNER-CORE
  • ACINETOBACTER-CALCOACETICUS
  • STRUCTURAL-CHARACTERIZATION
  • LIPOPOLYSACCHARIDE
  • OLIGOSACCHARIDE
  • BURKHOLDERIA
  • POLYSACCHARIDE
  • FRAGMENTS
  • EFFICIENT
  • STRATEGY

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