ASYMMETRIC-SYNTHESIS OF 2'-PHOSPHONOMETHYL(3',4'-DIHYDROXYBUTYL)CYTOSINE AND 2'-PHOSPHONOMETHYL(3',4'-DIHYDROXYBUTYL)GUANINE NUCLEOTIDES

Authors
EVANS CA HEWGILL RT MANSOUR TS
Citation
Ca. Evans et al., ASYMMETRIC-SYNTHESIS OF 2'-PHOSPHONOMETHYL(3',4'-DIHYDROXYBUTYL)CYTOSINE AND 2'-PHOSPHONOMETHYL(3',4'-DIHYDROXYBUTYL)GUANINE NUCLEOTIDES, Tetrahedron : asymmetry, 8(14), 1997, pp. 2299-2302
Citations number
11
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
8
Issue
14
Year of publication
1997
Pages
2299 - 2302
Database
ISI
SICI code
0957-4166(1997)8:14<2299:AO2>2.0.ZU;2-0
Abstract
The synthesis of 2'-phosphonomethyl(3',4'-dihydroxylbutyl nucleotides of cytosine and guanine 13 and 15 possessing the 2'S,3'S absolute conf iguration was readily accomplished in eleven and ten steps respectivel y from L-ascorbic acid via the protected tetrols 9 and 8. Alcohol 8 un dergoes efficiently a regiospecific Mitsunobu coupling with 6-chloro-2 -aminopurine to furnish the N-9 isomer which was further transformed t o 15. (C) 1997 Elsevier Science Ltd.