Light-induced O-glycosylation of unprotected deoxythioglycosyl donors

Mayuka Nakanishi; Daisuke Takahashi; Kazunobu Toshima

doi:10.1039/c3ob41143e

Light-induced O-glycosylation of unprotected deoxythioglycosyl donors

Mayuka Nakanishi, Daisuke Takahashi, Kazunobu Toshima

Department of Applied Chemistry

Research output: Contribution to journal › Article › peer-review

37 Citations (Scopus)

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.

Original language	English
Pages (from-to)	5079-5082
Number of pages	4
Journal	Organic and Biomolecular Chemistry
Volume	11
Issue number	31
DOIs	https://doi.org/10.1039/c3ob41143e
Publication status	Published - 2013 Aug 21

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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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.",

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Light-induced O-glycosylation of unprotected deoxythioglycosyl donors

Abstract

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