1,2-cis-α-Stereoselective Glycosylation Utilizing a Glycosyl-Acceptor-Derived Borinic Ester and Its Application to the Total Synthesis of Natural Glycosphingolipids

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23 Citations (Scopus)

Abstract

1,2-cis-α-Stereoselective glycosylations were conducted using a 1,2-anhydroglucose donor and mono-ol acceptors in the presence of a glycosyl-acceptor-derived borinic ester. Reactions proceeded smoothly under mild conditions to provide the corresponding α-glycosides with high stereoselectivity in moderate to high yields. In addition, the present method was applied successfully to the direct glycosylation of a protected ceramide acceptor and the total synthesis of natural glycosphingolipids (GSLs).

Original languageEnglish
Pages (from-to)5030-5033
Number of pages4
JournalOrganic Letters
Volume18
Issue number19
DOIs
Publication statusPublished - 2016 Oct 7

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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