Chirospecific synthesis of D and Lp-chlorohomophenylalanine N-t-BOC DCHA salts
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.
KeywordsAmino acids Chirospecific D-Glucosamine hydrochloride D-Mannosamine hydrochloride L-N-t-Butyloxycarbonylserinal D-N-t-Butyloxycarbonylserinal D-p-Chlorohomophenylalanine N-t-Boc DCHA salt L-p-Chlorohomophenylalanine N-t-Boc DCHA salt
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