Photo-induced glycosylation using a diaryldisulfide as an organo-Lewis photoacid catalyst

Naoto Iibuchi; Takahiro Eto; Manabu Aoyagi; Reiji Kurinami; Hayato Sakai; Taku Hasobe; Daisuke Takahashi; Kazunobu Toshima

doi:10.1039/C9OB02674F

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Photo-induced glycosylation using a diaryldisulfide as an organo-Lewis photoacid catalyst†

Naoto Iibuchi,^a Takahiro Eto,^a Manabu Aoyagi,^a Reiji Kurinami,^a Hayato Sakai,^b Taku Hasobe,

^b Daisuke Takahashi

*^a and Kazunobu Toshima

*^a

Author affiliations

* Corresponding authors

^a Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan
E-mail: dtak@applc.keio.ac.jp, toshima@applc.keio.ac.jp
Fax: +81 45-566-1576

^b Department of Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan

Abstract

Photo-induced glycosylations of several acceptors with trichloroacetimidate donors using bis(2-naphthyl)disulfide as an organo-Lewis photoacid (LPA) catalyst proceeded effectively to give the corresponding glycosides in good to high yields. In addition, the ground and excited state absorption spectra of bis(2-naphthyl)disulfide with or without NEt₃ suggested the Lewis acidity of bis(2-naphthyl)disulfide upon photo-irradiation.

This article is part of the themed collections: Glycosylation: New methodologies and applications and Synthetic methodology in OBC

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Article information

DOI: https://doi.org/10.1039/C9OB02674F
Article type: Communication
Submitted: 17 12 2019
Accepted: 09 1 2020
First published: 09 1 2020

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Org. Biomol. Chem., 2020,18, 851-855

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Photo-induced glycosylation using a diaryldisulfide as an organo-Lewis photoacid catalyst

N. Iibuchi, T. Eto, M. Aoyagi, R. Kurinami, H. Sakai, T. Hasobe, D. Takahashi and K. Toshima, Org. Biomol. Chem., 2020, 18, 851 DOI: 10.1039/C9OB02674F

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Organic & Biomolecular Chemistry

Photo-induced glycosylation using a diaryldisulfide as an organo-Lewis photoacid catalyst†

Abstract

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Photo-induced glycosylation using a diaryldisulfide as an organo-Lewis photoacid catalyst

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