Synthesis of 2′,3′-Dideoxy-3′-fluorothymidine Using Individual Anomers of 1,5-Di-O-benzoyl-2,3-dideoxy-3-fluoro-D-erythro-pentofuranose as Glycosylating Agents

Igor A. Mikhailopulo; Tamara I. Pricota; Nicolai E. Poopeiko; Tatjana V. Klenitskaya; Natalia B. Khripach

doi:10.1055/s-1993-25925

Synthesis 1993; 1993(7): 700-704
DOI: 10.1055/s-1993-25925

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Synthesis of 2′,3′-Dideoxy-3′-fluorothymidine Using Individual Anomers of 1,5-Di-O-benzoyl-2,3-dideoxy-3-fluoro-D-erythro-pentofuranose as Glycosylating Agents

Igor A. Mikhailopulo^* , Tamara I. Pricota, Nicolai E. Poopeiko, Tatjana V. Klenitskaya, Natalia B. Khripach

^*Institute of Bio-Organic Chemistry, Byelorussian Academy of Sciences, 220600 Minsk, Zhodinskaya, 5/2, Byelorussia

Abstract

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A convenient preparation of α- and β-anomers of 1,5-di-O-benzoyl-2, 3-dideoxy-3-fluoro-D-erythro-pentofuranose is described. Each anomer is studied as the glycosylating agent in the reaction with bis-trimethylsilylated thymine in the presence of trimethylsilyl triflate. Under optimum conditions, 2′,3′-dideoxy-3′-fluorothymidine (FLT) and its α-anomer are isolated in 64 and 25% yields, respectively.

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