Stereocontrolled Photoinduced Glycosylation Using an Aryl Thiourea as an Organo photoacid

Tomoya Kimura, Takahiro Eto, Daisuke Takahashi, Kazunobu Toshima

Research output: Contribution to journalArticle

36 Citations (Scopus)

Abstract

Photoinduced glycosylation of alcohols with α-glucosyl trichloroacetimidates, using aryl urea and thioureas as organo photoacids, was examined under long wavelength UV (ultraviolet) irradiation. The results show, for the first time, that such glycosylations proceed effectively to give the corresponding glycosides in high yields. In addition, high β-stereoselectivity was obtained under high concentration conditions, whereas high α-stereoselectivity was realized under low concentration conditions.

Original languageEnglish
Pages (from-to)3190-3193
Number of pages4
JournalOrganic Letters
Volume18
Issue number13
DOIs
Publication statusPublished - 2016 Jul 1

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Glycosylation
Stereoselectivity
Thiourea
thioureas
glucosides
Glycosides
ureas
Urea
low concentrations
alcohols
Alcohols
Irradiation
Wavelength
irradiation
wavelengths
trichloroacetamide

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Stereocontrolled Photoinduced Glycosylation Using an Aryl Thiourea as an Organo photoacid. / Kimura, Tomoya; Eto, Takahiro; Takahashi, Daisuke; Toshima, Kazunobu.

In: Organic Letters, Vol. 18, No. 13, 01.07.2016, p. 3190-3193.

Research output: Contribution to journalArticle

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