SYNTHESIS OF 2',3'-DIDEOXY-3'-HYDROXYMETHYLCYTIDINE - A UNIQUE ANTIVIRAL NUCLEOSIDE

Authors
FAUL MM HUFF BE DUNLAP SE FRANK SA FRITZ JE KALDOR SW LETOURNEAU ME STASZAK MA WARD JA WERNER JA WINNEROSKI LL
Citation
Mm. Faul et al., SYNTHESIS OF 2',3'-DIDEOXY-3'-HYDROXYMETHYLCYTIDINE - A UNIQUE ANTIVIRAL NUCLEOSIDE, Tetrahedron, 53(24), 1997, pp. 8085-8104
Citations number
59
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
24
Year of publication
1997
Pages
8085 - 8104
Database
ISI
SICI code
0040-4020(1997)53:24<8085:SO2-AU>2.0.ZU;2-W
Abstract
The synthesis of 2',3'-dideoxy-3'-hydroxymethylcytidine 1 was accompli shed using two different approaches. First, uridine and cytidine were used to prepare the key intermediate epoxides 15 and 31 which were ope ned with cyanide, deoxygenated by elimination to vinyl nitriles 17 and 36, and reduced by 1,4 hydride addition to the saturated nitriles 18 and 37. Secondly, a novel Rh-catalyzed hydroformylation reaction of 2' ,3'-didehydro-2',3'-dideoxycytidine 46 was used to prepare 1 in four s teps. The attempted use of 2'-deoxyuridine and 2'-deoxycytidine to pre pare 1 is also discussed. (C) 1997 Elsevier Science Ltd.