Solid phase synthesis of 1,3,4,7-tetrasubstituted perhydro-1,4-diazepine-2,5-diones

被引：53

作者：

Nefzi, A ^{[1
]}

Ostresh, JM ^{[1
]}

Houghten, RA ^{[1
]}

机构：

[1] TORREY PINES INST MOL STUDIES,SAN DIEGO,CA 92121

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 28期

关键词：

D O I：

10.1016/S0040-4039(97)01086-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The solid phase synthesis of 1,3,4,7-tetrasubstituted perhydro-1,4-diazepine-2,5-diones is described. Starting from the resin-bound tBu ester of aspartic acid and employing reductive alkylation and amide formation, 40 diazepines have been synthesized in good yield and high purity. The general nature of this approach permits not only large numbers of individual diazepines to be prepared, but also combinatorial libraries. (C) 1997 Elsevier Science Ltd.

引用

页码：4943 / 4946

页数：4

共 10 条

[1] Barany G., 1979, PEPTIDES A, V2, P1
[2] ADVANTAGEOUS APPLICATIONS OF AZABENZOTRIAZOLE (TRIAZOLOPYRIDINE)-BASED COUPLING REAGENTS TO SOLID-PHASE PEPTIDE-SYNTHESIS
CARPINO, LA
EL-FAHAM, A
MINOR, CA
ALBERICIO, F
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (02) : 201 - 203
[3] AN EFFECTIVE SYNTHESIS OF N-(9-FLUORENYLMETHYLOXYCARBONYL) ALPHA-AMINO ALDEHYDES FROM S-BENZYL THIOESTERS
HO, PT
NGU, KY
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (08) : 2313 - 2316
[4] HOUGHTEN RA, 1986, INT J PEPT PROT RES, V27, P673
[5] GENERAL-METHOD FOR THE RAPID SOLID-PHASE SYNTHESIS OF LARGE NUMBERS OF PEPTIDES - SPECIFICITY OF ANTIGEN-ANTIBODY INTERACTION AT THE LEVEL OF INDIVIDUAL AMINO-ACIDS
HOUGHTEN, RA
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1985, 82 (15) : 5131 - 5135
[6] Krchnak V., 1996, MOL DIVERSITY COMBIN, P99
[7] Solid phase synthesis of heterocyclic compounds from linear peptides: Cyclic ureas and thioureas
Nefzi, A
Ostresh, JM
Meyer, JP
Houghten, RA
[J]. TETRAHEDRON LETTERS, 1997, 38 (06) : 931 - 934
[8] The current status of heterocyclic combinatorial libraries
Nefzi, A
Ostresh, JM
Houghten, RA
[J]. CHEMICAL REVIEWS, 1997, 97 (02) : 449 - 472
[9] PEPTIDE LIBRARIES - DETERMINATION OF RELATIVE REACTION-RATES OF PROTECTED AMINO-ACIDS IN COMPETITIVE COUPLINGS
OSTRESH, JM
WINKLE, JH
HAMASHIN, VT
HOUGHTEN, RA
[J]. BIOPOLYMERS, 1994, 34 (12) : 1681 - 1689
[10] Enantiospecific synthesis of heterocycles from alpha-amino acids
Sardina, FJ
Rapoport, H
[J]. CHEMICAL REVIEWS, 1996, 96 (06) : 1825 - 1872

← 1 →