Stereocontrolled Synthesis of Phenolic α-d-Glycopyranosides

Gabrielle St-Pierre; Laila Dafik; Ellen Klegraf; Stephen Hanessian

doi:10.1055/s-0035-1561461

Synthesis, Table of Contents

Synthesis 2016; 48(20): 3575-3588
DOI: 10.1055/s-0035-1561461

paper

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

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Abstract

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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.

Key words

aryl glycoside - stereocontrolled glycosidation - minimal protection - 1,2-cis d-glycopyranoside - phenyl sialoside

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References

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Supplementary Material

Supporting Information