Stereoselective epimerizations of glycosyl thiols

Paul Murphy

doi:http://hdl.handle.net/10379/7082

Stereoselective epimerizations of glycosyl thiols

Paul Murphy

Infectious Disease

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

Abstract

Glycosyl thiols are widely used in stereoselective S-glycoside synthesis. Their epimerization from 1,2-trans to 1,2-cis thiols (e.g., equatorial to axial epimerization in thioglucopyranose) was attained using TiCl4, while SnCl4 promoted their axial-to-equatorial epimerization. The method included application for stereoselective #946;-d-manno- and #946;-l-rhamnopyranosyl thiol formation. Complex formation explains the equatorial preference when using SnCl4, whereas TiCl4 can shift the equilibrium toward the 1,2-cis thiol via 1,3-oxathiolane formation.

Original language	English (Ireland)
Journal	Organic Letters
Volume	19
DOIs	https://doi.org/http://hdl.handle.net/10379/7082
Publication status	Published - 1 Oct 2017

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Authors
Lisa M. Doyle, Shane OSullivan, Claudia Di Salvo, Michelle McKinney, Patrick McArdle and Paul V. Murphy

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title = "Stereoselective epimerizations of glycosyl thiols",

abstract = "Glycosyl thiols are widely used in stereoselective S-glycoside synthesis. Their epimerization from 1,2-trans to 1,2-cis thiols (e.g., equatorial to axial epimerization in thioglucopyranose) was attained using TiCl4, while SnCl4 promoted their axial-to-equatorial epimerization. The method included application for stereoselective \#946;-d-manno- and \#946;-l-rhamnopyranosyl thiol formation. Complex formation explains the equatorial preference when using SnCl4, whereas TiCl4 can shift the equilibrium toward the 1,2-cis thiol via 1,3-oxathiolane formation.",

author = "Paul Murphy",

year = "2017",

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doi = "http://hdl.handle.net/10379/7082",

language = "English (Ireland)",

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AU - Murphy, Paul

PY - 2017/10/1

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N2 - Glycosyl thiols are widely used in stereoselective S-glycoside synthesis. Their epimerization from 1,2-trans to 1,2-cis thiols (e.g., equatorial to axial epimerization in thioglucopyranose) was attained using TiCl4, while SnCl4 promoted their axial-to-equatorial epimerization. The method included application for stereoselective #946;-d-manno- and #946;-l-rhamnopyranosyl thiol formation. Complex formation explains the equatorial preference when using SnCl4, whereas TiCl4 can shift the equilibrium toward the 1,2-cis thiol via 1,3-oxathiolane formation.

AB - Glycosyl thiols are widely used in stereoselective S-glycoside synthesis. Their epimerization from 1,2-trans to 1,2-cis thiols (e.g., equatorial to axial epimerization in thioglucopyranose) was attained using TiCl4, while SnCl4 promoted their axial-to-equatorial epimerization. The method included application for stereoselective #946;-d-manno- and #946;-l-rhamnopyranosyl thiol formation. Complex formation explains the equatorial preference when using SnCl4, whereas TiCl4 can shift the equilibrium toward the 1,2-cis thiol via 1,3-oxathiolane formation.

U2 - http://hdl.handle.net/10379/7082

DO - http://hdl.handle.net/10379/7082

M3 - Article

VL - 19

JO - Organic Letters

JF - Organic Letters

ER -

Stereoselective epimerizations of glycosyl thiols

Abstract

Authors (Note for portal: view the doc link for the full list of authors)

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