ISSN:
1438-2199
Schlagwort(e):
Amino 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
Quelle:
Springer Online Journal Archives 1860-2000
Thema:
Medizin
Notizen:
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.
Materialart:
Digitale Medien
URL:
http://dx.doi.org/10.1007/BF00808125
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