title: Chirospecific synthesis of D and Lp-chlorohomophenylalanine N-t-BOC DCHA salts.
abstract: The chirospecific conversions of D-glucosamine hydrochloride and D-mannosamine hydrochloride to the configurationally stable L and D isomers of N-t-butyloxycarbonylserinal were carried out byt-butylcarbonylation followed by sodium borohydride reduction and sodium meta-periodate oxidation. Reaction of the L and D aldehydes with the Wittig reagent prepared from 4-chlorobenzyltriphenylphosphonium chloride and butyl lithium followed by catalytic hydrogenation, Jones oxidation and salt formation with dicyclohexylamine gave the DCHA salts of the D and L isomers ofp-chlorohomophenylalanine N-t-Boc in high enatiomeric excess. The optical purity of the title compounds was established by hydrolysis to the respective free amino acids, followed by chiral derivatization and HPLC analysis.
authors.affiliation: Department of Organic Chemistry, Southwest Foundation for Biomedical Research, P.O. Box 28147, 78228-0147, San Antonio, TX, USA.
authors.forename: J W
authors.initials: JW
authors.lastname: Cessac
authors.forename: P N
authors.initials: PN
authors.lastname: Rao
authors.forename: H K
authors.initials: HK
authors.lastname: Kim