One-Step Stereocontrolled Synthesis of α-Anomeric Carboxylic Acid Esters from Unprotected Glycosyl Donors: A Water-Soluble Aspirin Pro-Drug Analogue­

Stephen  Hanessian; Vincent  Mascitti; Pu-Ping  Lu; Hideki  Ishida

doi:10.1055/s-2002-34372

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Synthesis 2002(14): 1959-1968
DOI: 10.1055/s-2002-34372

PAPER

One-Step Stereocontrolled Synthesis of α-Anomeric Carboxylic Acid Esters from Unprotected Glycosyl Donors: A Water-Soluble Aspirin Pro-Drug Analogue

Stephen Hanessian*, Vincent Mascitti, Pu-Ping Lu, Hideki Ishida
Department of Chemistry, Université de Montréal, C. P. 6128, Succ. Centre-Ville, Montréal, P. Q., H3C 3J7, Canada
Fax: +(514)3435728; e-Mail: stephen.hanessian@umontreal.ca;

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Publication History

Received 16 April 2002
Publication Date:
26 September 2002 (online)

Abstract
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Abstract

The reaction of 2-(3-methoxypyridyl) β-d-gluco- and d-galactopyranosides with various carboxylic acids affords the corresponding α-1-esters in high yields. Aspirin can be solubilized in water as the α-d-galactopyranosyl ester.

Key words

carbohydrates - aspirin - pro-drugs - esters - stereoselectivity

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