Synthesis 2016; 48(20): 3575-3588
DOI: 10.1055/s-0035-1561461
paper
© Georg Thieme Verlag Stuttgart · New York

Stereocontrolled Synthesis of Phenolic α-d-Glycopyranosides

Gabrielle St-Pierre
Department of Chemistry, Université de Montréal, PO Box 6128, Succ., Centre-ville, Montréal, Québec, H3C 3J7, Canada   Email: stephen.hanessian@umontreal.ca
,
Laila Dafik
Department of Chemistry, Université de Montréal, PO Box 6128, Succ., Centre-ville, Montréal, Québec, H3C 3J7, Canada   Email: stephen.hanessian@umontreal.ca
,
Ellen Klegraf
Department of Chemistry, Université de Montréal, PO Box 6128, Succ., Centre-ville, Montréal, Québec, H3C 3J7, Canada   Email: stephen.hanessian@umontreal.ca
,
Stephen Hanessian*
Department of Chemistry, Université de Montréal, PO Box 6128, Succ., Centre-ville, Montréal, Québec, H3C 3J7, Canada   Email: stephen.hanessian@umontreal.ca
› Author Affiliations
Further Information

Publication History

Received: 04 April 2016

Accepted after revision: 25 April 2016

Publication Date:
14 June 2016 (eFirst)

Dedicated to Professor Richard Schmidt for his seminal contributions to glycoside synthesis

Abstract

Adopting the ‘remote activation concept’ toward stereocontrolled glycoside synthesis with minimal use of protection groups, a general synthesis of phenolic 1,2-cis glycopyranosides is reported, as exemplified by aryl α-d-galacto-, α-d-gluco- and 2-azido α-d-glucopyranosides among others using glycosyl donors bearing an anomeric (3-bromo-2-pyridyloxy) group and catalyzed by methyl triflate.

Supporting Information

 
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