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

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

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...

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Bibliographic Details
Main Authors: DUSAN MILJKOVIC, VELIMIR POPSAVIN, MIRJANA POPSAVIN, STEVAN LAJSIC, GORDANA CETKOVIC
Format: Article
Language:English
Published: Serbian Chemical Society 2002-01-01
Series:Journal of the Serbian Chemical Society
Subjects:
3'-deoxythymidine
dethioacetalization
N-glycosylation
modified nucleosides
D-xylose
Online Access:http://www.shd.org.yu/HtDocs/SHD/Vol67/No1/V67-No1-01.pdf
Description
Summary: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.
ISSN:0352-5139

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