4.6 Article

Light-induced O-glycosylation of unprotected deoxythioglycosyl donors

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 11, Issue 31, Pages 5079-5082

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c3ob41143e

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Funding

  1. MEXT
  2. Ministry of Education, Culture, Sports, Science and Technology of Japan (MEXT)
  3. Grants-in-Aid for Scientific Research [23310153, 24102528] Funding Source: KAKEN

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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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