Development of novel glycosyl donors for 1,2-cis glycosylation reaction for amino sugar and synthesis of anti-Helicobacter pylori oligosaccharide

Shino Manabe, Kazuyuki Ishii, Yukishige Ito

Research output: Contribution to journalShort survey

9 Citations (Scopus)

Abstract

Despite advances in synthetic carbohydrate chemistry, the 1,2-cis-selective glycosylation reaction of 2-deoxy-2-amino sugars has not progressed during the last three decades. For such glycosylations, 2-azide glycosyl donors have been extensively employed, notwithstanding difficulties in their preparation and moderate selectivities. Herein, we report on a highly 1,2-cis-selective trans-carbamate sugar donor, which can be readily prepared in high yields. Furthermore, the utility of the novel cis-selective glycosyl donor for preparing complex oligosaccharides is demonstrated through the effective synthesis of an anti-Helicobacter pylori hexasaccharide.

Original languageEnglish
Pages (from-to)187-202
Number of pages16
JournalTrends in Glycoscience and Glycotechnology
Volume20
Issue number114
DOIs
Publication statusPublished - 2008 Sep 1
Externally publishedYes

Keywords

  • Amino sugar
  • Anti-Helicobacter pylori oligosaccharide
  • Glycosylaion reaction
  • Selectivity
  • Trans-carbamate having donor

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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