Diastereoselective desymmetric 1,2-cis-glycosylation of meso-diols via chirality transfer from a glycosyl donor

Masamichi Tanaka; Koji Sato; Ryoki Yoshida; Nobuya Nishi; Rikuto Oyamada; Kazuki Inaba; Daisuke Takahashi; Kazunobu Toshima

doi:10.1038/s41467-020-16365-8

Nature Communications (May 2020)

Diastereoselective desymmetric 1,2-cis-glycosylation of meso-diols via chirality transfer from a glycosyl donor

Masamichi Tanaka,
Koji Sato,
Ryoki Yoshida,
Nobuya Nishi,
Rikuto Oyamada,
Kazuki Inaba,
Daisuke Takahashi,
Kazunobu Toshima

Affiliations

Masamichi Tanaka: Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi
Koji Sato: Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi
Ryoki Yoshida: Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi
Nobuya Nishi: Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi
Rikuto Oyamada: Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi
Kazuki Inaba: Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi
Daisuke Takahashi: Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi
Kazunobu Toshima: Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi

DOI: https://doi.org/10.1038/s41467-020-16365-8
Journal volume & issue: Vol. 11, no. 1
pp. 1 – 10

Abstract

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Enzyme-catalyzed desymmetric glycosylations are often found in nature, however the corresponding chemical methods are lacking. Here, the authors report a highly diastereoselective desymmetric 1,2-cis-glycosylation of meso-diols found in myo-inositol 1,3,5-orthoesters using a boronic acid catalyst.

Published in Nature Communications

ISSN: 2041-1723 (Online)
Publisher: Nature Portfolio
Country of publisher: United Kingdom
LCC subjects: Science
Website: https://www.nature.com/ncomms/

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