SYNTHESIS OF MESO-2',3'-DIDEOXY-3'BETA-HYDROXYMETHYL CARBOCYCLIC NUCLEOSIDES AS POTENTIAL ANTIVIRAL DRUGS - UNUSUAL COMPETITIVE 2-O-VERSUS N-1-ALKYLATION OF 3-SUBSTITUTED PYRIMIDINES UNDER MITSUNOBU CONDITIONS

Authors
BONNAL C CHAVIS C LUCAS M
Citation
C. Bonnal et al., SYNTHESIS OF MESO-2',3'-DIDEOXY-3'BETA-HYDROXYMETHYL CARBOCYCLIC NUCLEOSIDES AS POTENTIAL ANTIVIRAL DRUGS - UNUSUAL COMPETITIVE 2-O-VERSUS N-1-ALKYLATION OF 3-SUBSTITUTED PYRIMIDINES UNDER MITSUNOBU CONDITIONS, Journal of the Chemical Society. Perkin transactions. I, (11), 1994, pp. 1401-1410
Citations number
53
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
11
Year of publication
1994
Pages
1401 - 1410
Database
ISI
SICI code
0300-922X(1994):11<1401:SOMCN>2.0.ZU;2-X
Abstract
The synthesis of meso-2',3'-dideoxy-3'beta-hydroxymethyl carbocyclic n ucleosides as potential antiviral drugs via the alkylation of protecte d purines and pyrimidines with meso-beta,beta'-disubstituted cyclopent anols under Mitsunobu conditions is described. Chemical evidence for a n unusual competitive 2-O vs. N-1-alkylation of 3-substituted pyrimidi nes is presented.