Diboron-Catalyzed Regio- And 1,2- cis-α-Stereoselective Glycosylation of trans-1,2-Diols

Shunpei Tomita, Masamichi Tanaka, Michitaka Inoue, Kazuki Inaba, Daisuke Takahashi, Kazunobu Toshima

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

Regio- and 1,2-cis-α-stereoselective glycosylations were investigated using 1,2-anhydroglucose donors and trans-1,2-diol sugar acceptors in the presence of a diboron catalyst. The reactions proceeded smoothly to provide the corresponding 1,2-cis-α-glycosides with consistently very high stereoselectivity and were regioselectivity controlled by the protecting groups of the acceptor. The present glycosylation method was applied successfully to the efficient synthesis of α-1,3-glucan pentasaccharide.

Original languageEnglish
Pages (from-to)16254-16262
Number of pages9
JournalJournal of Organic Chemistry
Volume85
Issue number24
DOIs
Publication statusPublished - 2020 Dec 18

ASJC Scopus subject areas

  • Organic Chemistry

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