Development and application of boronic-acid-catalyzed regioselective and 1,2-cis-stereoselective glycosylation

Research output: Contribution to journalArticle

Abstract

1,2-cis-Glycosides are frequently found in many biologically active natural products and pharmaceutical compounds. Therefore, to elucidate the precise biological roles of these carbohydrates and structure-activity relationships, the development of efficient glycosylation methods for the stereoselective synthesis of 1,2-cis-glycosides is becoming increasingly important in synthetic organic chemistry. In this review article, development of boronic-acid-catalyzed regioselective and 1,2-cis-stereoselective glycosylation that was recently developed in our laboratory, is introduced. This glycosylation method was successfully applied to the regioselective and stereoselective formation of 1,2-cis-β-glycosidic linkages, to the efficient synthesis of complex glycosides, and to the direct regioselective and 1,2-cis-stereoselective glycosylation of unprotected glycosides. Furthermore, mechanistic studies were consistent with a highly dissociative concerted SNi mechanism.

Original languageEnglish
Pages (from-to)221-231
Number of pages11
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume78
Issue number3
DOIs
Publication statusPublished - 2020 Jan 1

Keywords

  • 1,2-Cis-glycoside
  • Borinic acid
  • Boronic acid
  • Direct modification
  • Glycosylation
  • Natural glycoside
  • Organoboron catalyst
  • Regioselective
  • Stereoselective
  • Unprotected glycoside

ASJC Scopus subject areas

  • Organic Chemistry

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