Boronic-acid-catalyzed regioselective and stereoselective glycosylations via sni-type mechanism

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Abstract

1,2-cis-Glycosides are frequently found in various biologically active natural products. However, the stereoselective synthesis of these glycosides is still difficult due to the lack of neighboring group participation. Therefore, the development of efficient synthetic methods has been required. In this context, we have reported novel regio-and 1,2-cis-α-stereoselective glycosylations using 1,2-anhydroglycosyl donors and diol acceptor-derived boronic ester catalysts without additives under mild conditions. In addition, development of 1,2-cis-stereoselective glycosylations using mono-ol acceptor-derived borinic esters and their application to the total synthesis of natural glycolipids were also reported. In this mini-review, further extended studies on boronic-acid-catalyzed regio-and stereoselective glycosylations are introduced.

Original languageEnglish
Pages (from-to)SE93-SE94
JournalTrends in Glycoscience and Glycotechnology
Volume31
Issue number181
DOIs
Publication statusPublished - 2019 Jul 1

Keywords

  • Borinic acid
  • Boronic acid
  • Glycosylation
  • Organoboron compound
  • Regioselective
  • Si-type mechanism
  • Stereoselective
  • Unprotected glycoside

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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