Issue 31, 2013
From the journal:

Organic & Biomolecular Chemistry

Light-induced O-glycosylation of unprotected deoxythioglycosyl donors†

Mayuka Nakanishi,a   Daisuke Takahashia  and  Kazunobu Toshima*a  

* 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: toshima@applc.keio.ac.jp
Fax: +81 45-566-1576

Abstract

The O-glycosylation of several unprotected deoxythioglycosides and alcohols using 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) under long-wavelength UV irradiation was effectively realized using a single electron transfer (SET) mechanism. In some cases, the use of p-methoxyboronic acid was very effective in temporary protection of the 1,3-diol (C4 and C6 positions) of the unprotected glycosyl donors to increase the yields of the obtained O-glycosides.

Graphical abstract: Light-induced O-glycosylation of unprotected deoxythioglycosyl donors

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Article information

DOI
https://doi.org/10.1039/C3OB41143E
Article type
Communication
Submitted
04 Jun 2013
Accepted
20 Jun 2013
First published
21 Jun 2013

Org. Biomol. Chem., 2013,11, 5079-5082

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Light-induced O-glycosylation of unprotected deoxythioglycosyl donors

M. Nakanishi, D. Takahashi and K. Toshima, Org. Biomol. Chem., 2013, 11, 5079 DOI: 10.1039/C3OB41143E

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