S-Benzimidazolyl (SBiz) Imidates As a Platform for Oligosaccharide Synthesis Via Active-Latent, Armed-Disarmed, Selective, and Orthogonal Activations

Overview

Journal J Org Chem

Publisher American Chemical Society

Specialty Chemistry

Date 2017 Jan 31

PMID 28135419

Citations 4

Authors

Scott J Hasty

Mithila D Bandara

Nigam P Rath

Alexei V Demchenko

Affiliations

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Abstract

This article describes the development of S-benzimidazolyl (SBiz) imidates as versatile building blocks for oligosaccharide synthesis. The SBiz imidates have been originally developed as a new platform for active-latent glycosylations. This article expands upon the utility of these compounds. The application to practically all common concepts for the expeditious oligosaccharide synthesis including selective, chemoselective, and orthogonal strategies is demonstrated. The strategy development was made possible thanks to our enhanced understanding of the reaction mechanism and the modes by which SBiz imidates interact with various promoters of glycosylation.

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