Armed-disarmed effect of remote protecting groups on the glycosylation reaction of 2,3-dideoxyglycosyl donors

Satoshi Tomono, Shunichi Kusumi, Daisuke Takahashi, Kazunobu Toshima

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

The armed-disarmed effect of remote protecting groups at the C-4 and/or C-6 position(s) on the glycosylation reactions of 2,3-dideoxyglycosyl donors was investigated. It was found that under various glycosylation conditions, 4- or 6-O-Bn 2,3-dideoxyglycosyl donors were much more reactive than the corresponding 4,6-di-O-Bz 2,3-dideoxyglycosyl donors. Based on these results, an effective and chemoselective glycosylation reaction using 4,6-di-O-Bn glycosyl acetate and 4-OH-6-O-Bz glycosyl acetate was realized, producing a 2,3-dideoxydisaccharide in good yield with high α-stereoselectivity.

Original languageEnglish
Pages (from-to)2399-2403
Number of pages5
JournalTetrahedron Letters
Volume52
Issue number18
DOIs
Publication statusPublished - 2011 May 4

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Glycosylation
Acetates
Stereoselectivity

Keywords

  • 2,3-Dideoxyglycosides
  • Armed-disarmed concept
  • Chemoselective glycosylation
  • Remote protecting group effect

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Armed-disarmed effect of remote protecting groups on the glycosylation reaction of 2,3-dideoxyglycosyl donors. / Tomono, Satoshi; Kusumi, Shunichi; Takahashi, Daisuke; Toshima, Kazunobu.

In: Tetrahedron Letters, Vol. 52, No. 18, 04.05.2011, p. 2399-2403.

Research output: Contribution to journalArticle

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