Novel 1,2-cis-stereoselective glycosylations utilizing organoboron reagents and their application to natural products and complex oligosaccharide synthesis

Daisuke Takahashi, Masamichi Tanaka, Nobuya Nishi, Kazunobu Toshima

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

In this mini-review article, 1,2-cis-stereoselective glycosylation methods utilizing organoboron reagents and 1,2-anhydroglycosyl donors that were developed in our laboratory, including regio- and 1,2-cis-stereoselective glycosylations using glycosyl-acceptor-derived boronic ester catalysts and 1,2-cis-stereoselective glycosylations using glycosyl-acceptor-derived borinic ester catalysts, are recounted. Representative applications of these methods to the synthesis of biologically active natural products and a complex oligosaccharide are also described.

Original languageEnglish
Pages (from-to)64-77
Number of pages14
JournalCarbohydrate Research
Volume452
DOIs
Publication statusPublished - 2017 Nov 27

Keywords

  • 1,2-cis-Glycoside
  • Borinic acid
  • Boronic acid
  • Glycosylation
  • Regioselective
  • Stereoselective

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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