N-benzyl-2,3-trans-carbamate-bearing glycosyl donors for 1,2-cis-selective glycosylation reactions

Shino Manabe, Kazuyuki Ishii, Yukishige Ito

Research output: Contribution to journalArticlepeer-review

28 Citations (Scopus)

Abstract

Glycosyl donors for the preparation of 1,2-cis glycosides of amino sugars have been developed. The 2,3-trans-cyclic-carbamate-carrying glycosyl donors were readily prepared from the corresponding known trichloroethyl carbamate protected amino sugars under standard hydroxy group benzylation conditions. The donors exhibit high 1,2-cis stereoselectivity towards secondary hydroxy group substrates. In the case of primary hydroxy acceptors, high stereoselectivities were achieved with the aid of the dioxane effect. After glycosylation, the carbamate was removed under alkaline conditions. Importantly, these glycosyl donors can be used in polymer-supported and solid-phase synthesis. Glycosyl donors for the preparation of 1,2-cis glycosides of amino sugars have been developed. The preparation of these donors, the scope and limitation of acceptors, and deprotection procedures are described. The glycosyl donors can be used in polymer-supported and solid-phase oligosaccharide synthesis.

Original languageEnglish
Pages (from-to)497-516
Number of pages20
JournalEuropean Journal of Organic Chemistry
Issue number3
DOIs
Publication statusPublished - 2011 Jan 1
Externally publishedYes

Keywords

  • Carbamates
  • Carbohydrates
  • Diastereoselectivity
  • Glycosylation
  • Solid-phase synthesis

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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