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Stereoselective acetylation of [1-(hydroxy)-4-(3-phenyl)butyl]phosphonic acid, diethyl ester
- Source :
- Tetrahedron: Asymmetry. 8:1055-1059
- Publication Year :
- 1997
- Publisher :
- Elsevier BV, 1997.
-
Abstract
- The chiral intermediate (S) [1-(acetoxyl)-4-(3-phenyl)butyl]phosphonic acid, diethyl ester 2 was prepared for the total synthesis of a squalene synthase inhibitor, BMS-188494. The stereoselective acetylation of racemic [1-(hydroxy)-4-(3-phenyl)butyl] phosphonic acid, diethyl ester 1 was carried out in toluene using lipase from Geotrichum candidum. Isopropenyl acetate was used as an acylating agent. A reaction yield of 38% and an optical purity of 95% were obtained for chiral 2.
- Subjects :
- biology
Chemistry
organic chemicals
Organic Chemistry
Total synthesis
Toluene
Catalysis
Inorganic Chemistry
Acylation
Isopropenyl acetate
Squalene
chemistry.chemical_compound
biology.protein
Organic chemistry
heterocyclic compounds
Stereoselectivity
Physical and Theoretical Chemistry
Lipase
Enantiomeric excess
Subjects
Details
- ISSN :
- 09574166
- Volume :
- 8
- Database :
- OpenAIRE
- Journal :
- Tetrahedron: Asymmetry
- Accession number :
- edsair.doi...........dd1e7cbd3e8c46af593727a182d3fd7f