An alternative strategy for the synthesis of 3′-azido-2′, 3′-dideoxy-4′-thionucleosides starting from d-xylose

B Tber, NE Fahmi, G Ronco, P Villa, DF Ewing…

Index: Tber; Fahmi; Ronco; Villa; Ewing; Mackenzie Carbohydrate Research, 1995 , vol. 267, # 2 p. 203 - 215

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Citation Number: 20

Abstract

Methyl 5-O-acetyl-3-azido-2, 3-dideoxy-4-thio-α, β-d-erythro-pentofuranoside and 1, 5-O- diacetyl-3-azido-2, 3-dideoxy-4-thio-α, β-d-erythro-pentofuranose were prepared in twelve and thirteen steps, respectively, by an efficient route starting from d-xylose. Both compounds were easily converted into an anomeric mixture of pyrimidine nucleosides by reaction with the 2, 4-bi (trimethylsilyloxy) derivative in the presence of a Lewis acid. The anomeric ...