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由1,2 -原酸酯合成糖基磷酸酯及其在原位糖基化反应中的应用。

Synthesis of glycosyl phosphates from 1,2-orthoesters and application to in situ glycosylation reactions.

作者信息

Ravidà Alessandra, Liu Xinyu, Kovacs Linda, Seeberger Peter H

机构信息

Laboratorium für Organische Chemie, Swiss Federal Institute of Technology, ETH Zürich, HCI F315, Wolfgang-Pauli Strasse 10, 8093 Zürich, Switzerland.

出版信息

Org Lett. 2006 Apr 27;8(9):1815-8. doi: 10.1021/ol0603155.

DOI:10.1021/ol0603155
PMID:16623558
Abstract

[reaction: see text] A series of glycosyl phosphates were prepared in high yield by treatment of the corresponding 1,2-orthoesters with dibutyl phosphate. Glycosyl phosphates are efficient glycosylating agents even when used in crude form or when generated in situ. The immunodominant epitope trirhamnoside of group B Streptococcus was prepared to demonstrate the synthetic utility of the method.

摘要

[反应:见正文] 通过用磷酸二丁酯处理相应的1,2-原酸酯,以高产率制备了一系列糖基磷酸酯。糖基磷酸酯即使以粗品形式使用或原位生成时也是有效的糖基化试剂。制备了B族链球菌的免疫显性表位三鼠李糖苷以证明该方法的合成实用性。

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