A CONVENIENT, LARGE-SCALE SYNTHESIS OF N-CBZ-(S-PHENYL)-L-CYSTEINE

被引:6
作者
MARZONI, G [1 ]
KALDOR, SW [1 ]
TRIPPE, AJ [1 ]
SHAMBLIN, BM [1 ]
FRITZ, JE [1 ]
机构
[1] ELI LILLY & CO,LILLY CORP CTR,LILLY RES LABS,INDIANAPOLIS,IN 46285
关键词
D O I
10.1080/00397919508015453
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N-Cbz-(S-phenyl)-L-cysteine (3) has been prepared on a multikilogram scale in high yield and optical purity from the beta-lactone of N-Cbz-L-serine.
引用
收藏
页码:2475 / 2482
页数:8
相关论文
共 14 条
[1]   CONVERSION OF SERINE BETA-LACTONES TO CHIRAL ALPHA-AMINO-ACIDS BY COPPER-CONTAINING ORGANOLITHIUM AND ORGANOMAGNESIUM REAGENTS [J].
ARNOLD, LD ;
DROVER, JCG ;
VEDERAS, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (15) :4649-4659
[2]   ASYMMETRIC-SYNTHESIS OF BETA-SUBSTITUTED ALPHA-AMINO-ACIDS VIA A CHIRAL NI-II COMPLEX OF DEHYDROALANINE [J].
BELOKON, YN ;
SAGYAN, AS ;
DJAMGARYAN, SM ;
BAKHMUTOV, VI ;
BELIKOV, VM .
TETRAHEDRON, 1988, 44 (17) :5507-5514
[3]   KINETIC RESOLUTION OF UNNATURAL AND RARELY OCCURRING AMINO-ACIDS - ENANTIOSELECTIVE HYDROLYSIS OF N-ACYL AMINO-ACIDS CATALYZED BY ACYLASE-I [J].
CHENAULT, HK ;
DAHMER, J ;
WHITESIDES, GM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (16) :6354-6364
[4]   S-ARYL-L-CYSTEINE S,S-DIOXIDES - DESIGN, SYNTHESIS, AND EVALUATION OF A NEW CLASS OF INHIBITORS OF KYNURENINASE [J].
DUA, RK ;
TAYLOR, EW ;
PHILLIPS, RS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (04) :1264-1270
[5]  
GOEL OP, 1993, ORG SYNTH COLL, V8, P68
[6]   POTENTIAL ANTICANCER AGENTS .5. SOME SULFUR-SUBSTITUTED DERIVATIVES OF CYSTEINE [J].
GOODMAN, L ;
ROSS, LO ;
BAKER, BR .
JOURNAL OF ORGANIC CHEMISTRY, 1958, 23 (09) :1251-1257
[7]   SYNTHESIS OF AROMATIC S-SUBSTITUTED DERIVATIVES OF N-ACETYL-L-CYSTEINE [J].
HICKMAN, RJS ;
CHRISTIE, BJ ;
GUY, RW ;
WHITE, TJ .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1985, 38 (06) :899-904
[8]  
KALDOR SW, 1994, 208TH NAT M AM CHEM
[9]   CHEMISTRY OF ORTHO-SILYLATED KETENE ACETALS - BIOMIMETIC SYNTHESIS OF CIS-BETA-LACTAMS [J].
KITA, Y ;
TAMURA, O ;
MIKI, T ;
TONO, H ;
SHIBATA, N ;
TAMURA, Y .
TETRAHEDRON LETTERS, 1989, 30 (06) :729-730
[10]   KETENE EQUIVALENTS .11. A FORMYLCARBONIUM ION SYNTHON - SYNTHESIS OF 3-THIO-SUBSTITUTED 2-AMINO ACIDS AND THIO-SUBSTITUTED ENAMINES FROM 2-ACYLOXYACRYLONITRILES [J].
OKU, A ;
HORIIE, N ;
HARADA, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1987, 60 (02) :609-612