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Synthesis 2005(15): 2476-2478  
DOI: 10.1055/s-2005-872079
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© Georg Thieme Verlag Stuttgart · New York

First Synthesis of 2,3,4-Tri-O-benzyl-5-thio-d-ribono-1,5-lactone

Ludovic Chaveriat, Imane Stasik*, Jérôme Lalot, Gilles Demailly, Daniel Beaupère
Laboratoire des Glucides, FRE 2779, Université de Picardie Jules Verne, 33 Rue Saint-Leu 80039 Amiens, France
Fax: +33(322)827560; e-Mail: imane.stasik@u-picardie.fr;
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Publication History

Received 24 March 2005
Publication Date:
20 July 2005 (online)

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Abstract

The first synthesis of 2,3,4-tri-O-benzyl-5-thio-d-ribono-1,5-lactone was achieved, in five steps, from 5-bromo-5-deoxy-d-ribono-1,4-lactone; displacement of the bromide group, in methyl 2,3,4-tri-O-benzyl-5-bromo-5-deoxy-d-ribonate (7), gave methyl 2,3,4-tri-O-benzyl-5-S-acetyl-5-thio-d-ribonate (10) in 96% yield. Saponification of compound 10 gave the methyl 2,3,4-tri-O-benzyl-5-thio-d-ribonic acid (11) in 98% yield. Treatment of 11 with DIC-HOBt as coupling reagents led, after cyclisation, the target compound, 2,3,4-tri-O-benzyl-5-thio-d-ribono-1,5-lactone (12) in 75% yield.

Key words

d-ribono-1,4-lactone - methyl 5-bromo-5-deoxy-d-ribonate - DIC-HOBt - 2,3,4-tri-O-benzyl-5-thio-d-ribono-1,5-lactone