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CHIROSPECIFIC SYNTHESIS OF AMINO-ACIDS, AMINO ALDEHYDES AND AMINO-ALCOHOLS FROM D-GLUCOSAMINE HYDROCHLORIDE - A MULTIGRAM SYNTHESIS OF N-BOC-L-SERINAL
被引:22
作者
:
GIANNIS, A
论文数:
0
引用数:
0
h-index:
0
机构:
Institut für Organische Chemie, Biochemie der Universität Bonn, 5300 Bonn 1
GIANNIS, A
HENK, T
论文数:
0
引用数:
0
h-index:
0
机构:
Institut für Organische Chemie, Biochemie der Universität Bonn, 5300 Bonn 1
HENK, T
机构
:
[1]
Institut für Organische Chemie, Biochemie der Universität Bonn, 5300 Bonn 1
来源
:
TETRAHEDRON LETTERS
|
1990年
/ 31卷
/ 09期
关键词
:
D O I
:
10.1016/S0040-4039(00)88778-X
中图分类号
:
O62 [有机化学];
学科分类号
:
070303 ;
081704 ;
摘要
:
N-tert.-butyloxycarbonyl-L-serinal 4 was readily prepared from D-glucosamine hydrochloride 1 in three steps. The versatile synthetic intermediate 4 is chemically and configurationally stable for prolonged time and reacts with various stabilized phosphorus ylides to produce the enantiomerically pure (ee < 95%) allylamino alcohols 6 in high yields. © 1990.
引用
收藏
页码:1253 / 1256
页数:4
相关论文
共 26 条
[1]
BALDWIN JE, 1989, TETRAHEDRON, V45, P6318
[2]
BARRETT GC, 1985, CHEM BIOCH AMINO ACI
[3]
A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS
CARLSEN, PHJ
论文数:
0
引用数:
0
h-index:
0
机构:
STANFORD UNIV, DEPT CHEM, STANFORD, CA 94305 USA
STANFORD UNIV, DEPT CHEM, STANFORD, CA 94305 USA
CARLSEN, PHJ
KATSUKI, T
论文数:
0
引用数:
0
h-index:
0
机构:
STANFORD UNIV, DEPT CHEM, STANFORD, CA 94305 USA
STANFORD UNIV, DEPT CHEM, STANFORD, CA 94305 USA
KATSUKI, T
MARTIN, VS
论文数:
0
引用数:
0
h-index:
0
机构:
STANFORD UNIV, DEPT CHEM, STANFORD, CA 94305 USA
STANFORD UNIV, DEPT CHEM, STANFORD, CA 94305 USA
MARTIN, VS
SHARPLESS, KB
论文数:
0
引用数:
0
h-index:
0
机构:
STANFORD UNIV, DEPT CHEM, STANFORD, CA 94305 USA
STANFORD UNIV, DEPT CHEM, STANFORD, CA 94305 USA
SHARPLESS, KB
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1981,
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: 3936
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3938
[4]
SYNTHESIS OF (2R,4S,5S)-5-ACETAMIDO-4-HYDROXY-PIPECOLINIC ACID AS A POTENTIAL INHIBITOR OF SIALIDASES
CLINCH, K
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV ZURICH,INST ORGAN CHEM,WINTERTHURERSTR 190,CH-8057 ZURICH,SWITZERLAND
CLINCH, K
VASELLA, A
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV ZURICH,INST ORGAN CHEM,WINTERTHURERSTR 190,CH-8057 ZURICH,SWITZERLAND
VASELLA, A
SCHAUER, R
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV ZURICH,INST ORGAN CHEM,WINTERTHURERSTR 190,CH-8057 ZURICH,SWITZERLAND
SCHAUER, R
[J].
TETRAHEDRON LETTERS,
1987,
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6428
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ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES
DALE, JA
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Stanford University, Stanford
DALE, JA
DULL, DL
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Stanford University, Stanford
DULL, DL
MOSHER, HS
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Stanford University, Stanford
MOSHER, HS
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1969,
34
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-
&
[6]
GARNER P, 1987, J ORG CHEM, V52, P2364
[7]
LANTHANOIDS IN ORGANIC-SYNTHESIS .6. THE REDUCTION OF ALPHA-ENONES BY SODIUM-BOROHYDRIDE IN THE PRESENCE OF LANTHANOID CHLORIDES - SYNTHETIC AND MECHANISTIC ASPECTS
GEMAL, AL
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV SCI & MED GRENOBLE,BATIMENT CHEM RECH,ETUD DYNAM & STRUCT SELECT,F-38041 GRENOBLE,FRANCE
UNIV SCI & MED GRENOBLE,BATIMENT CHEM RECH,ETUD DYNAM & STRUCT SELECT,F-38041 GRENOBLE,FRANCE
GEMAL, AL
LUCHE, JL
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV SCI & MED GRENOBLE,BATIMENT CHEM RECH,ETUD DYNAM & STRUCT SELECT,F-38041 GRENOBLE,FRANCE
UNIV SCI & MED GRENOBLE,BATIMENT CHEM RECH,ETUD DYNAM & STRUCT SELECT,F-38041 GRENOBLE,FRANCE
LUCHE, JL
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1981,
103
(18)
: 5454
-
5459
[8]
FRAGMENTATION AND WITTIG OLEFINATION OF GLUCOSAMINE DERIVATIVES - A SIMPLE ROUTE TO OPEN-CHAIN AMINO-SUGARS AND CHIRAL GLYCEROLS
GIANNIS, A
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV BONN,INST ORGAN CHEM & BIOCHEM,GERHARD DOMAGK STR 1,D-5300 BONN 1,FED REP GER
UNIV BONN,INST ORGAN CHEM & BIOCHEM,GERHARD DOMAGK STR 1,D-5300 BONN 1,FED REP GER
GIANNIS, A
MUNSTER, P
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV BONN,INST ORGAN CHEM & BIOCHEM,GERHARD DOMAGK STR 1,D-5300 BONN 1,FED REP GER
UNIV BONN,INST ORGAN CHEM & BIOCHEM,GERHARD DOMAGK STR 1,D-5300 BONN 1,FED REP GER
MUNSTER, P
SANDHOFF, K
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV BONN,INST ORGAN CHEM & BIOCHEM,GERHARD DOMAGK STR 1,D-5300 BONN 1,FED REP GER
UNIV BONN,INST ORGAN CHEM & BIOCHEM,GERHARD DOMAGK STR 1,D-5300 BONN 1,FED REP GER
SANDHOFF, K
STEGLICH, W
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV BONN,INST ORGAN CHEM & BIOCHEM,GERHARD DOMAGK STR 1,D-5300 BONN 1,FED REP GER
UNIV BONN,INST ORGAN CHEM & BIOCHEM,GERHARD DOMAGK STR 1,D-5300 BONN 1,FED REP GER
STEGLICH, W
[J].
TETRAHEDRON,
1988,
44
(23)
: 7177
-
7180
[9]
2-O-BENZYLGLYCERALDEHYDE - A SYNTHETIC BUILDING BLOCK AVAILABLE IN BOTH ENANTIOMERIC FORMS AND CONFIGURATIONALLY STABLE OWING TO RAPID OLIGOMERIZATION
JAGER, V
论文数:
0
引用数:
0
h-index:
0
JAGER, V
WEHNER, V
论文数:
0
引用数:
0
h-index:
0
WEHNER, V
[J].
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
1989,
28
(04)
: 469
-
470
[10]
Jager V., 1989, ANGEW CHEM, V101, P512
←
1
2
3
→
共 26 条
[1]
BALDWIN JE, 1989, TETRAHEDRON, V45, P6318
[2]
BARRETT GC, 1985, CHEM BIOCH AMINO ACI
[3]
A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS
CARLSEN, PHJ
论文数:
0
引用数:
0
h-index:
0
机构:
STANFORD UNIV, DEPT CHEM, STANFORD, CA 94305 USA
STANFORD UNIV, DEPT CHEM, STANFORD, CA 94305 USA
CARLSEN, PHJ
KATSUKI, T
论文数:
0
引用数:
0
h-index:
0
机构:
STANFORD UNIV, DEPT CHEM, STANFORD, CA 94305 USA
STANFORD UNIV, DEPT CHEM, STANFORD, CA 94305 USA
KATSUKI, T
MARTIN, VS
论文数:
0
引用数:
0
h-index:
0
机构:
STANFORD UNIV, DEPT CHEM, STANFORD, CA 94305 USA
STANFORD UNIV, DEPT CHEM, STANFORD, CA 94305 USA
MARTIN, VS
SHARPLESS, KB
论文数:
0
引用数:
0
h-index:
0
机构:
STANFORD UNIV, DEPT CHEM, STANFORD, CA 94305 USA
STANFORD UNIV, DEPT CHEM, STANFORD, CA 94305 USA
SHARPLESS, KB
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1981,
46
(19)
: 3936
-
3938
[4]
SYNTHESIS OF (2R,4S,5S)-5-ACETAMIDO-4-HYDROXY-PIPECOLINIC ACID AS A POTENTIAL INHIBITOR OF SIALIDASES
CLINCH, K
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV ZURICH,INST ORGAN CHEM,WINTERTHURERSTR 190,CH-8057 ZURICH,SWITZERLAND
CLINCH, K
VASELLA, A
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV ZURICH,INST ORGAN CHEM,WINTERTHURERSTR 190,CH-8057 ZURICH,SWITZERLAND
VASELLA, A
SCHAUER, R
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV ZURICH,INST ORGAN CHEM,WINTERTHURERSTR 190,CH-8057 ZURICH,SWITZERLAND
SCHAUER, R
[J].
TETRAHEDRON LETTERS,
1987,
28
(51)
: 6425
-
6428
[5]
ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES
DALE, JA
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Stanford University, Stanford
DALE, JA
DULL, DL
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Stanford University, Stanford
DULL, DL
MOSHER, HS
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Stanford University, Stanford
MOSHER, HS
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1969,
34
(09)
: 2543
-
&
[6]
GARNER P, 1987, J ORG CHEM, V52, P2364
[7]
LANTHANOIDS IN ORGANIC-SYNTHESIS .6. THE REDUCTION OF ALPHA-ENONES BY SODIUM-BOROHYDRIDE IN THE PRESENCE OF LANTHANOID CHLORIDES - SYNTHETIC AND MECHANISTIC ASPECTS
GEMAL, AL
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV SCI & MED GRENOBLE,BATIMENT CHEM RECH,ETUD DYNAM & STRUCT SELECT,F-38041 GRENOBLE,FRANCE
UNIV SCI & MED GRENOBLE,BATIMENT CHEM RECH,ETUD DYNAM & STRUCT SELECT,F-38041 GRENOBLE,FRANCE
GEMAL, AL
LUCHE, JL
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV SCI & MED GRENOBLE,BATIMENT CHEM RECH,ETUD DYNAM & STRUCT SELECT,F-38041 GRENOBLE,FRANCE
UNIV SCI & MED GRENOBLE,BATIMENT CHEM RECH,ETUD DYNAM & STRUCT SELECT,F-38041 GRENOBLE,FRANCE
LUCHE, JL
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1981,
103
(18)
: 5454
-
5459
[8]
FRAGMENTATION AND WITTIG OLEFINATION OF GLUCOSAMINE DERIVATIVES - A SIMPLE ROUTE TO OPEN-CHAIN AMINO-SUGARS AND CHIRAL GLYCEROLS
GIANNIS, A
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV BONN,INST ORGAN CHEM & BIOCHEM,GERHARD DOMAGK STR 1,D-5300 BONN 1,FED REP GER
UNIV BONN,INST ORGAN CHEM & BIOCHEM,GERHARD DOMAGK STR 1,D-5300 BONN 1,FED REP GER
GIANNIS, A
MUNSTER, P
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV BONN,INST ORGAN CHEM & BIOCHEM,GERHARD DOMAGK STR 1,D-5300 BONN 1,FED REP GER
UNIV BONN,INST ORGAN CHEM & BIOCHEM,GERHARD DOMAGK STR 1,D-5300 BONN 1,FED REP GER
MUNSTER, P
SANDHOFF, K
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV BONN,INST ORGAN CHEM & BIOCHEM,GERHARD DOMAGK STR 1,D-5300 BONN 1,FED REP GER
UNIV BONN,INST ORGAN CHEM & BIOCHEM,GERHARD DOMAGK STR 1,D-5300 BONN 1,FED REP GER
SANDHOFF, K
STEGLICH, W
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV BONN,INST ORGAN CHEM & BIOCHEM,GERHARD DOMAGK STR 1,D-5300 BONN 1,FED REP GER
UNIV BONN,INST ORGAN CHEM & BIOCHEM,GERHARD DOMAGK STR 1,D-5300 BONN 1,FED REP GER
STEGLICH, W
[J].
TETRAHEDRON,
1988,
44
(23)
: 7177
-
7180
[9]
2-O-BENZYLGLYCERALDEHYDE - A SYNTHETIC BUILDING BLOCK AVAILABLE IN BOTH ENANTIOMERIC FORMS AND CONFIGURATIONALLY STABLE OWING TO RAPID OLIGOMERIZATION
JAGER, V
论文数:
0
引用数:
0
h-index:
0
JAGER, V
WEHNER, V
论文数:
0
引用数:
0
h-index:
0
WEHNER, V
[J].
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
1989,
28
(04)
: 469
-
470
[10]
Jager V., 1989, ANGEW CHEM, V101, P512
←
1
2
3
→