Document Type

Article

Keywords

carbohydrates, glycosylation, ICS-28, oligosaccharides, synthesis

Abstract

This article describes the development of alkylated S-benzimidazolyl (SBiz) imidates as versatile building blocks for chemical glycosylation. The SBiz imidates have been originally developed as a new platform for active-latent glycosylations and its utility was further extended to other common strategies for oligosaccharide synthesis. This article expands upon the utility of these compounds. We developed a general protocol for the synthesis of a series of N-alkylated SBiz glycosides from N-protected SBiz aglycones by Lewis acid-mediated coupling with glucose pentaacetate. The N-alkylated SBiz moiety was found to be stable under strong basic conditions which allowed us to obtain both armed and disarmed N-alkylated SBiz donors. These donors showed good reactivity at a variety of activation conditions, and generally provided high yields in glycosylations.

Publication Date

September 2017

Publication Title

Pure Applied Chemistry

Volume

89

Issue

9

First Page

1321

Last Page

1331

Comments


10.1515/pac-2017-0112

DOI

10.1515/pac-2017-0112

Download

Share

COinS