Summary
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.
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Cessac, J.W., Rao, P.N. & Kim, H.K. Chirospecific synthesis of D and Lp-chlorohomophenylalanine N-t-BOC DCHA salts. Amino Acids 6, 97–105 (1994). https://doi.org/10.1007/BF00808125
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DOI: https://doi.org/10.1007/BF00808125