NEW SYNTHETIC ROUTES FOR THE PREPARATION OF 2'-C-METHYLENE NUCLEOSIDES

Authors
WOLF J MONNERET C PONTIKIS R FLORENT JC
Citation
J. Wolf et al., NEW SYNTHETIC ROUTES FOR THE PREPARATION OF 2'-C-METHYLENE NUCLEOSIDES, EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, (11), 1998, pp. 2417-2423
Citations number
31
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY → ACNP
ISSN journal
1434193X
Issue
11
Year of publication
1998
Pages
2417 - 2423
Database
ISI
SICI code
1434-193X(1998):11<2417:NSRFTP>2.0.ZU;2-K
Abstract
Two new routes to 2',3'-dideoxy-2'-C-methylene nucleoside analogs have been developed. The first is based upon the coupling reaction of a 1- O-acetyl 2-C-(methylphenylsulfinyl) sugar with a silylated base under Vorbruggen conditions, followed by thermal elimination of phenylsulfin ic acid. The second route involved a condensation of a silylated base with a (pi-allyl)palladium complex derived from a 2-C-acetoxy-methyl f uranoid glycal.