Light-induced O-glycosylation of unprotected deoxythioglycosyl donors

Research output: Contribution to journalArticle

26 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 languageEnglish
Pages (from-to)5079-5082
Number of pages4
JournalOrganic and Biomolecular Chemistry
Volume11
Issue number31
DOIs
Publication statusPublished - 2013 Aug 21

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Glycosylation
glucosides
quinones
Glycosides
electron transfer
alcohols
Alcohols
Irradiation
Electrons
Light
Wavelength
acids
irradiation
Acids
wavelengths
benzoquinone

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 journalArticle

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