An efficient de novo synthesis of 3’-deoxythymidine from D-xylose

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-b-D-ribofuranose (5), followed by the stereospecific coupling of the intermediate 5 with silylated thymine, in the presence of ethylaluminium dichloride as the catalyst.

Keywords

• 3'-deoxythymidine
• dethioacetalization
• N-glycosylation
• modified nucleosides
• D-xylose