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Issue 31, 2013
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Light-induced O-glycosylation of unprotected deoxythioglycosyl donors

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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.

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

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Publication details

The article was received on 04 Jun 2013, accepted on 20 Jun 2013 and first published on 21 Jun 2013


Article type: Communication
DOI: 10.1039/C3OB41143E
Citation: 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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