A NEW SYNTHETIC EQUIVALENT OF THE GLUTAMIC-ACID GAMMA-ANION AND ITS APPLICATION TO THE SYNTHESIS OF S-(+)-GAMMA-CARBOXYGLUTAMIC ACID

被引：30
作者：
ATTWOOD, MR
CARR, MG
JORDAN, S
机构：
[1] Roche Products Limited, Welwyn Garden City
来源：
TETRAHEDRON LETTERS | 1990年 / 31卷 / 02期
关键词：
D O I：
10.1016/S0040-4039(00)94393-4
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Protected S-pyroglutamic acid can be deprotonated specifically at the γ-position. The resulting enolate can be converted into γ-carboxyglutamic acid in optically pure form. © 1990.
引用
收藏
页码：283 / 284
页数：2
相关论文
共 16 条
[1]   STEREOSPECIFIC AMINO-ACID SYNTHESIS - PREPARATION OF THE GAMMA-ANION DERIVED FROM GLUTAMIC-ACID [J].
BALDWIN, JE ;
NORTH, M ;
FLINN, A ;
MOLONEY, MG .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (12) :828-829
[2]   SYNTHESIS OF NONPROTEINOGENIC AMINO-ACIDS .2. PREPARATION OF A SYNTHETIC EQUIVALENT OF THE GAMMA-ANION SYNTHON FOR ASYMMETRIC AMINO-ACID SYNTHESIS [J].
BALDWIN, JE ;
NORTH, M ;
FLINN, A ;
MOLONEY, MG .
TETRAHEDRON, 1989, 45 (05) :1453-1464
[3]   SYNTHESIS OF NONPROTEINOGENIC AMINO-ACIDS .3. CONVERSION OF GLUTAMIC-ACID INTO GAMMA,DELTA-UNSATURATED ALPHA-AMINO-ACIDS [J].
BALDWIN, JE ;
NORTH, M ;
FLINN, A ;
MOLONEY, MG .
TETRAHEDRON, 1989, 45 (05) :1465-1474
[4]   AMINO-ACIDS AND PEPTIDES .188. ENZYMATIC RESOLUTION OF GAMMA-CARBOXY-DL-GLUTAMIC ACID [J].
CEROVSKY, V ;
JOST, K .
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1984, 49 (11) :2562-2565
[5]   SIMPLE SYNTHESIS OF L-GAMMA-CARBOXYGLUTAMATE AND DERIVATIVES THEREOF [J].
DANISHEFSKY, S ;
BERMAN, E ;
CLIZBE, LA ;
HIRAMA, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (15) :4385-4386
[6]   A MILD 2-STEP METHOD FOR THE HYDROLYSIS METHANOLYSIS OF SECONDARY AMIDES AND LACTAMS [J].
FLYNN, DL ;
ZELLE, RE ;
GRIECO, PA .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (14) :2424-2426
[7]  
FLYNN DL, 1968, CHEM BER, V101, P41
[8]  
MACHEREY, CHIRALPLATE
[9]   D(-)-GAMMA-CARBOXYGLUTAMIC AND L(+)-GAMMA-CARBOXYGLUTAMIC ACID (GLA) - RESOLUTION OF SYNTHETIC GLA DERIVATIVES [J].
MARKI, W ;
OPPLIGER, M ;
THANEI, P ;
SCHWYZER, R .
HELVETICA CHIMICA ACTA, 1977, 60 (03) :798-806
[10]   NEW APPROACHES TO THE ASYMMETRIC-SYNTHESIS OF NON-PROTEINOGENIC ALPHA-AMINO-ACIDS AND DIPEPTIDES THROUGH CHIRAL BETA-LACTAM INTERMEDIATES [J].
OJIMA, I ;
CHEN, HJC ;
QIU, XG .
TETRAHEDRON, 1988, 44 (17) :5307-5318
12