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 | |
| Publication status | Published - 2013 Aug 21 |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
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Nakanishi, M., Takahashi, D., & Toshima, K. (2013). Light-induced O-glycosylation of unprotected deoxythioglycosyl donors. Organic and Biomolecular Chemistry, 11(31), 5079-5082. https://doi.org/10.1039/c3ob41143e