[1,2]-Wittig rearrangement of acetal systems: A highly stereocontrolled conversion of O-glycosides to C-glycosides

Katsuhiko Tomooka, H. Yamamoto, T. Nakai

Research output: Contribution to journalArticle

65 Citations (Scopus)

Abstract

We envisioned that acetal systems such as O-glycosides would undergo the [1,2]-Wittig shift with great facility owing to the relatively large stability of the α-oxy radical, together with retention of the anomeric configuration. We now wish to report that the [1,2]-Wittig rearrangement of O-glycosides proceeds with efficient stereocontrol over both the anomeric center and the new chiral center formed on the side chain to give the stereo-defined C-glycosides in high yields. We have demonstrated that the [1,2]-Wittig rearrangement of O-glycosides proceeds with efficient stereocontrol over both the anomeric center and the side-chain chiral center to give a novel class of the stereo-defined C-glycosides which is otherwise difficult to obtain.

Original languageEnglish
Pages (from-to)3317-3318
Number of pages2
JournalJournal of the American Chemical Society
Volume118
Issue number13
DOIs
Publication statusPublished - Apr 3 1996
Externally publishedYes

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Glycosides
Acetals
C-glycoside

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

[1,2]-Wittig rearrangement of acetal systems : A highly stereocontrolled conversion of O-glycosides to C-glycosides. / Tomooka, Katsuhiko; Yamamoto, H.; Nakai, T.

In: Journal of the American Chemical Society, Vol. 118, No. 13, 03.04.1996, p. 3317-3318.

Research output: Contribution to journalArticle

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