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

Shino Manabe, Kazuyuki Ishii, Yukishige Ito

研究成果: Article査読

29 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)497-516
ページ数20
ジャーナルEuropean Journal of Organic Chemistry
3
DOI
出版ステータスPublished - 2011 1 1
外部発表はい

ASJC Scopus subject areas

  • 物理化学および理論化学
  • 有機化学

フィンガープリント

「N-benzyl-2,3-trans-carbamate-bearing glycosyl donors for 1,2-cis-selective glycosylation reactions」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル