Issue 21, 2003

A novel method for the synthesis of 4′-thiopyrimidine nucleosides using hypervalent iodine compounds

Abstract

The coupling reactions of cyclic sulfides with a silylated pyrimidine nucleobase using a hypervalent iodine reagent were investigated. The reaction of silylated uracil with cyclic sulfide 12 using PhI[double bond, length as m-dash]O gave the desired β-anomer 14 in moderate yield. 4′-Thiouridine (22) was obtained by deprotection of 14.

Graphical abstract: A novel method for the synthesis of 4′-thiopyrimidine nucleosides using hypervalent iodine compounds

Article information

Article type
Paper
Submitted
20 May 2003
Accepted
10 Sep 2003
First published
01 Oct 2003

Org. Biomol. Chem., 2003,1, 3692-3697

A novel method for the synthesis of 4′-thiopyrimidine nucleosides using hypervalent iodine compounds

N. Nishizono, R. Baba, C. Nakamura, K. Oda and M. Machida, Org. Biomol. Chem., 2003, 1, 3692 DOI: 10.1039/B305644A

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