Regioselective and 1,2-cis-α-Stereoselective Glycosylation Utilizing Glycosyl-Acceptor-Derived Boronic Ester Catalyst

Akira Nakagawa, Masamichi Tanaka, Shun Hanamura, Daisuke Takahashi, Kazunobu Toshima

Research output: Contribution to journalArticle

38 Citations (Scopus)

Abstract

Regioselective and 1,2-cis-α-stereoselective glycosylations using 1α,2α-anhydro glycosyl donors and diol glycosyl acceptors in the presence of a glycosyl-acceptor-derived boronic ester catalyst. The reactions proceed smoothly to give the corresponding 1,2-cis-α-glycosides with high stereo- and regioselectivities in high yields without any further additives under mild reaction conditions. In addition, the present glycosylation method was successfully applied to the synthesis of an isoflavone glycoside.

Original languageEnglish
Pages (from-to)10935-10939
Number of pages5
JournalAngewandte Chemie - International Edition
Volume54
Issue number37
DOIs
Publication statusPublished - 2015 Sep 1

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Glycosylation
Glycosides
Esters
Stereoselectivity
Regioselectivity
Catalysts
Isoflavones

Keywords

  • boron
  • glycosylation
  • regioselectivity
  • stereoselectivity
  • synthetic methods

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis

Cite this

Regioselective and 1,2-cis-α-Stereoselective Glycosylation Utilizing Glycosyl-Acceptor-Derived Boronic Ester Catalyst. / Nakagawa, Akira; Tanaka, Masamichi; Hanamura, Shun; Takahashi, Daisuke; Toshima, Kazunobu.

In: Angewandte Chemie - International Edition, Vol. 54, No. 37, 01.09.2015, p. 10935-10939.

Research output: Contribution to journalArticle

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