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 |
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ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
- Biochemistry
Cite this
Light-induced O-glycosylation of unprotected deoxythioglycosyl donors. / Nakanishi, Mayuka; Takahashi, Daisuke; Toshima, Kazunobu.
In: Organic and Biomolecular Chemistry, Vol. 11, No. 31, 21.08.2013, p. 5079-5082.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Light-induced O-glycosylation of unprotected deoxythioglycosyl donors
AU - Nakanishi, Mayuka
AU - Takahashi, Daisuke
AU - Toshima, Kazunobu
PY - 2013/8/21
Y1 - 2013/8/21
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=84880630051&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84880630051&partnerID=8YFLogxK
U2 - 10.1039/c3ob41143e
DO - 10.1039/c3ob41143e
M3 - Article
VL - 11
SP - 5079
EP - 5082
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
SN - 1477-0520
IS - 31
ER -