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

Gordana Ćetković | Zendy; S. LAJSIC | Zendy; Mirjana Popsavin | Zendy; Velimir Popsavin | Zendy; Dušan Miljković | Zendy

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

Author(s) -

Gordana Ćetković,

S. LAJSIC,

Mirjana Popsavin,

Velimir Popsavin,

Dušan Miljković

Publication year - 2002

Publication title -

journal of the serbian chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.227

H-Index - 45

eISSN - 1820-7421

pISSN - 0352-5139

DOI - 10.2298/jsc0201001c

Subject(s) - stereospecificity , xylose , chemistry , thymine , catalysis , combinatorial chemistry , stereochemistry , organic chemistry , biochemistry , fermentation , dna

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-β-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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