Abstract
An efficient stereospecific synthesis of 3?-deoxythymidine has been achieved, starting from D-xylose. The key step of the synthesis involved the NBS promoted conversion of 5-O-benzoyl-2,3-di-S-ethyl-2,3-dithio-D-ribose diethyl dithioacetal (4) into the 1-O-acetyl-5-O-benzoyl-2,3-di-S-ethyl-2,3-dithio-?-D-ribofuranose (5) followed by the stereospecific coupling of the intermediate 5 with silylated thymine, in the presence of ethylaluminium dichloride as the catalyst.
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