The 2-N,N-Dibenzylamino Group As a Participating Group in the Synthesis of β-Glycosides

Overview

Journal Angew Chem Int Ed Engl

Specialty Chemistry

Date 2018 May 2

PMID 29711657

Citations 6

Authors

Hailong Jiao

Ole Hindsgaul

Affiliations

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Abstract

The novel glycosyl donor 2-N,N-dibenzylaminothioglycoside 1 reacts with glycopyranoside alcohols 2, presumably via intermediate 3, to provide 1,2-trans-linked disaccharides 4 in high yield (78-86 %) and with high stereoselectivity. The N-benzyl protecting groups are readily cleaved under normal hydrogenolysis conditions, facilitating the synthesis of oligosaccharides with free amino groups.

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