A DIASTEREOSELECTIVE SYNTHESIS OF LPHA-FLUORO-2,2-DIMETHYL-1,3-DIOXOLANE-4-PROPANOIC ACID METHYL-ESTER, A KEY INTERMEDIATE FOR THE PREPARATION OF ANTI-HIV EFFECTIVE FLUORODIDEOXYNUCLEOSIDES

Authors
SIDDIQUI MA MARQUEZ VE DRISCOLL JS BARCHI JJ
Citation
Ma. Siddiqui et al., A DIASTEREOSELECTIVE SYNTHESIS OF LPHA-FLUORO-2,2-DIMETHYL-1,3-DIOXOLANE-4-PROPANOIC ACID METHYL-ESTER, A KEY INTERMEDIATE FOR THE PREPARATION OF ANTI-HIV EFFECTIVE FLUORODIDEOXYNUCLEOSIDES, Tetrahedron letters, 35(20), 1994, pp. 3263-3266
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
20
Year of publication
1994
Pages
3263 - 3266
Database
ISI
SICI code
0040-4039(1994)35:20<3263:ADSOL>2.0.ZU;2-8
Abstract
lpha-fluoro-2,2-dimethyl-1,3-dioxolane-4-propanoic acid methyl ester ( 10), a key intermediate for the preparation of anti-HIV active (2,3-di deoxy-2-fluoro-beta-D-threo-pentofuranosyl) adenine (1, FddA) and eoxy -2-fluoro-beta-D-threo-pentofuranosyl)cytosine (2, FddC) was prepared via the diastereoselective fluorination of the chiral imide enolate ob tained from 8 with N-fluorobenzenesulfonimide. The overall yield of 10 from the readily available 1,2:5,6-di-O-isopropylidene-D-mannitol was 25% (de 93%).