STEREOSELECTIVE ACETYLATION OF [1-(HYDROXY)-4-(3-PHENYL)BUTYL]PHOSPHONIC ACID, DIETHYL ESTER

Authors
PATEL RN BANERJEE A SZARKA LJ
Citation
Rn. Patel et al., STEREOSELECTIVE ACETYLATION OF [1-(HYDROXY)-4-(3-PHENYL)BUTYL]PHOSPHONIC ACID, DIETHYL ESTER, Tetrahedron : asymmetry, 8(7), 1997, pp. 1055-1059
Citations number
25
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
8
Issue
7
Year of publication
1997
Pages
1055 - 1059
Database
ISI
SICI code
0957-4166(1997)8:7<1055:SAO[>2.0.ZU;2-M
Abstract
The chiral intermediate (S) [1-(acetoxyl)-4-(3-phenyl)butyl]phosphonic acid, diethyl ester 2 was prepared for the total synthesis of a squal ene synthase inhibitor, BMS-188494. The stereoselective acetylation of racemic [1-(hydroxy)-4-(3-phenyl)butyl] phosphonic acid, diethyl este r 1 was carried out in toluene using lipase from Geotrichum candidum. Isopropenyl acetate was used as an acylating agent. A reaction yield o f 38% and an optical purity of 95% were obtained for chiral 2. (C) 199 7 Elsevier Science Ltd.