Efficient synthesis of the four diastereomers of phosphothreonine from lactaldehyde

被引：28

作者：

Bongini, A

Camerini, R

Panunzio, M

机构：

[1] UNIV BOLOGNA,DIPARTIMENTO CHIM G CIAMICIAN,I-40126 BOLOGNA,ITALY

[2] CSFM,CNR,I-40126 BOLOGNA,ITALY

来源：

TETRAHEDRON-ASYMMETRY | 1996年 / 7卷 / 05期

关键词：

D O I：

10.1016/0957-4166(96)00164-4

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The four stereoisomers of phosphothreonine are obtained in high diastereomeric purity based on the stereoselective addition of trimethylsilyldiethylphosphite (TMSDEP) to scalemic N-trimethylsilyl-lacticimine and addition of TMSDEP to lactaldehyde followed by Mitsunobu inversion of the corresponding alpha-hydroxy-beta-silyloxy phosphonate. Copyright (C) 1996 Elsevier Science Ltd

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页码：1467 / 1476

页数：10

相关论文

共 80 条

[1] SYNTHESIS OF ORGANOPHOSPHORUS COMPOUNDS VIA SILYL ESTERS OF PHOSPHORUS-ACIDS [J].

AFARINKIA, K ;

REES, CW ;

CADOGAN, JIG .

TETRAHEDRON, 1990, 46 (20) :7175-7196

[2] NOVEL RENIN INHIBITORS - SYNTHESIS OF AMINOSTATINE AND COMPARISON WITH STATINE-CONTAINING ANALOGS [J].

ARROWSMITH, RJ ;

CARTER, K ;

DANN, JG ;

DAVIES, DE ;

HARRIS, CJ ;

MORTON, JA ;

LISTER, P ;

ROBINSON, JA ;

WILLIAMS, DJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (10) :755-757

[3] SYNTHESIS OF CARBAPENEMS VIA METALLOIMINES-ESTER ENOLATES CONDENSATION - A NEW SYNTHESIS OF (+)-1-BETA-METHYL PS-5 [J].

BANDINI, E ;

CAINELLI, G ;

GIACOMINI, D ;

MARTELLI, G ;

PANUNZIO, M ;

SPUNTA, G .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (11) :2347-2350

[4] SILICON-DIRECTED ASYMMETRIC-SYNTHESIS OF (IR, 2S)-(-)-(1,2-EPOXYPROPYL)PHOSPHONIC ACID (FOSFOMYCIN) FROM (S)-LACTALDEHYDE [J].

BANDINI, E ;

MARTELLI, G ;

SPUNTA, G ;

PANUNZIO, M .

TETRAHEDRON-ASYMMETRY, 1995, 6 (09) :2127-2130

[5]

BANDINI E, 1996, IN PRESS NATO ASI CH

[6] DIASTEREOSELECTIVITY IN THE ALKYLATION OF CHIRAL 2-AMINOMETHYL-1,3,2-DIOXAPHOSPHORINANE 2-OXIDES [J].

BARTLETT, PA ;

MCLAREN, KL .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1987, 33 (1-2) :1-14

[7]

BARTLETT PA, 1987, J MED CHEM, V30, P1603

[8] 1-AMINOALKYLPHOSPHONOUS ACIDS .1. ISOSTERES OF THE PROTEIN AMINO-ACIDS [J].

BAYLIS, EK ;

CAMPBELL, CD ;

DINGWALL, JG .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (12) :2845-2853

[9]

BENANI YL, 1993, SYNLETT, P35

[10]

BENNANI YL, 1990, TETRAHEDRON LETT, V31, P6461

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