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

31 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

Access to Document

10.1039/c3ob41143e

Fingerprint Dive into the research topics of 'Light-induced O-glycosylation of unprotected deoxythioglycosyl donors'. Together they form a unique fingerprint.

Cite this

@article{994a3d164d864b88836ff6731b458d3b,

title = "Light-induced O-glycosylation of unprotected deoxythioglycosyl donors",

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.",

author = "Mayuka Nakanishi and Daisuke Takahashi and Kazunobu Toshima",

year = "2013",

month = aug,

day = "21",

doi = "10.1039/c3ob41143e",

language = "English",

volume = "11",

pages = "5079--5082",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "31",

}

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

C2 - 23824170

AN - SCOPUS:84880630051

VL - 11

SP - 5079

EP - 5082

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 31

ER -

Light-induced O-glycosylation of unprotected deoxythioglycosyl donors

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Cite this