A facile and practical synthesis of peracylated 4-thio-D-ribofuranoses from D-glucose.

J Org Chem

Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, China

Published: March 2008

A practical synthesis of a peracylated 4-thio-D-ribofuranose 14 starting from inexpensive d-glucose is described. The C2-C6 portion of D-glucose was utilized, in which sulfur was introduced to C5 in two consecutive displacement reactions with net retention of configuration under mild conditions.

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http://dx.doi.org/10.1021/jo7026596DOI Listing

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