An improved synthesis of aziridine-2,3-dicarboxylates via azido alcohols - epimerization studies

被引：31

作者：

Breuning, A ^{[1
]}

Vicik, R ^{[1
]}

Schirmeister, T ^{[1
]}

机构：

[1] Univ Wurzburg, Inst Pharm & Food Chem, D-97074 Wurzburg, Germany

来源：

TETRAHEDRON-ASYMMETRY | 2003年 / 14卷 / 21期

关键词：

D O I：

10.1016/j.tetasy.2003.09.015

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The reasons for epimerization of 3-azido-2-hydroxysuccinates observed during the ring opening of epoxides or cyclic sulfites with sodium azide is now clarified. It is caused by the high acidity of the proton at the 3-position. This is proven by a proton deuterium exchange in assays with either D2O or DCl containing solvents. The anti-3-azido-2-hydroxysuccinates serve as intermediates for enantiomerically pure trans-aziridine-2,3-dicarboxylates for which an optimized synthetic pathway is presented. The first example of an enantiomerically pure mixed diester of the aziridine-2,3-dicarboxylic acid the synthesis of the allyl ethyl ester is reported herein. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：3301 / 3312

页数：12

共 46 条

[1]

ALBECK A, 2000, BIOCHEM J, V1, P71

[2] A FACILE ACCESS TO (R)-MALIC ACID [J].

ALPEGIANI, M ;

HANESSIAN, S .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (02) :278-279

[3] TOTAL SYNTHESES OF PENICILLANIC ACID S,S-DIOXIDE AND 6-AMINOPENICILLANIC ACID USING (BENZYLOXY)NITROMETHANE [J].

BARRETT, AGM ;

SAKADARAT, S .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (17) :5110-5117

[4] L-TRANS-EPOXYSUCCINYL-LEUCYLAMIDO(4-GUANIDINO)BUTANE (E-64) AND ITS ANALOGS AS INHIBITORS OF CYSTEINE PROTEINASES INCLUDING CATHEPSINS B, H AND L [J].

BARRETT, AJ ;

KEMBHAVI, AA ;

BROWN, MA ;

KIRSCHKE, H ;

KNIGHT, CG ;

TAMAI, M ;

HANADA, K .

BIOCHEMICAL JOURNAL, 1982, 201 (01) :189-198

[5]

BARRETT AJ, 1981, ACTA BIOL MED GER, V40, P1513

[6]

BERLIN K, 1968, TETRAHEDRON LETT, V7, P873

[7] Selective targeting of lysosomal cysteine proteases with radiolabeled electrophilic substrate analogs [J].

Bogyo, M ;

Verhelst, S ;

Bellingard-Dubouchaud, V ;

Toba, S ;

Greenbaum, D .

CHEMISTRY & BIOLOGY, 2000, 7 (01) :27-38

[8] ALKENES FROM CYCLIC SULFATES AND THIONOCARBONATES OF 1,2-DIOLS VIA TELLURIUM CHEMISTRY [J].

CHAO, B ;

MCNULTY, KC ;

DITTMER, DC .

TETRAHEDRON LETTERS, 1995, 36 (40) :7209-7212

[9] STEREOCHEMICAL COURSE OF 5-LIPOXYGENATION OF ARACHIDONATE BY RAT BASOPHIL LEUKEMIC-CELL (RBL-1) AND POTATO ENZYMES [J].

COREY, EJ ;

LANSBURY, PT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (12) :4093-4094

[10] Binding modes of a new epoxysuccinyl-peptide inhibitor of cysteine proteases.: Where and how do cysteine proteases express their selectivity? [J].

Czaplewski, C ;

Grzonka, Z ;

Jaskólski, M ;

Kasprzykowski, F ;

Kozak, M ;

Politowska, E ;

Ciarkowski, J .

BIOCHIMICA ET BIOPHYSICA ACTA-PROTEIN STRUCTURE AND MOLECULAR ENZYMOLOGY, 1999, 1431 (02) :290-305

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