An efficient and facile three-step synthesis of 5-amino-5-deoxy-D-pentonolactams from unprotected D-pentono-1,4-lactones.

被引：18

作者：

Bouchez, V ^{[1
]}

Stasik, I ^{[1
]}

Beaupere, D ^{[1
]}

Uzan, R ^{[1
]}

机构：

[1] UNIV PICARDIE,CHIM ORGAN LAB,F-80039 AMIENS,FRANCE

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 44期

关键词：

D O I：

10.1016/S0040-4039(97)10065-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Regioselective bromination of D-pentono-1,4-lactones with SOBr2 in DMF led to 5-bromo-5-deoxy derivatives. These intermediates were treated with LiN3 and hydrogenated to give 5-amino-5-deoxy-D-pentonolactams in 60-83% overall yield. (C) 1997 Elsevier Science Ltd.

引用

收藏

页码：7733 / 7736

页数：4

相关论文

共 11 条

[1] AMINO-ACIDS AND AMINO-SUGARS FROM BROMODEOXYALDONOLACTONES .8. [J].

BOCK, K ;

LUNDT, I ;

PEDERSEN, C .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1987, 41 (06) :435-441

[2] ALPHA-AMINO POLYHYDROXY TETRONIC AND PENTONIC ACIDS FROM BROMODEOXYALDONOLACTONES .9. [J].

BOLS, M ;

LUNDT, I .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1988, 42 (02) :67-74

[3] SYNTHESIS OF (2S,3R,4R)-3,4-DIHYDROXYPROLINE FROM 2,5-DIBROMO-2,5-DIDEOXY-D-XYLONO-1,4-LACTONE OR 2,5-DIBROMO-2,5-DIDEOXY-D-LYXONO-1,4-LACTONE [J].

BOLS, M ;

LUNDT, I .

ACTA CHEMICA SCANDINAVICA, 1992, 46 (03) :298-300

[4] EINE METHODE ZUR KATALYSIERTEN HERSTELLUNG VON CARBONSAURE UND SULFOSAURE-CHLORIDEN MIT THIONYLCHLORID [J].

BOSSHARD, HH ;

MORY, R ;

SCHMID, M ;

ZOLLINGER, H .

HELVETICA CHIMICA ACTA, 1959, 42 (05) :1653-1658

[5] Regioselective halogenation of pentono-1,4-lactones. Efficient synthesis of 5-chloro- and 5-bromo-5-deoxy derivatives [J].

Bouchez, V ;

Stasik, I ;

Beaupere, D ;

Uzan, R .

CARBOHYDRATE RESEARCH, 1997, 300 (02) :139-142

[6]

FLEET GWJ, 1990, TETRAHEDRON, V45, P319

[7] A new efficient way to alpha,omega-diaminoitols by direct azidation of unprotected itols. [J].

Glacon, V ;

ElMeslouti, A ;

Uzan, R ;

Demailly, G ;

Beaupere, D .

TETRAHEDRON LETTERS, 1996, 37 (21) :3683-3686

[8] Synthesis of 5-amino-5-deoxypentonolactams. [J].

Kefurt, K ;

Kefurtova, Z ;

Markova, V ;

Slivova, K .

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1996, 61 (07) :1027-1036

[9] SYNTHESIS OF 1,5-DIDEOXY-1,5-IMINO-D-XYLONOLACTAM VIA ACID-CATALYZED INTRAMOLECULAR SCHMIDT REARRANGEMENT [J].

NORRIS, P ;

HORTON, D ;

LEVINE, BR .

TETRAHEDRON LETTERS, 1995, 36 (43) :7811-7814

[10] Two efficient routes for construction of amidine-linked pseudo-disaccharide [J].

Suzuki, K ;

Fujii, T ;

Sato, K ;

Hashimoto, H .

TETRAHEDRON LETTERS, 1996, 37 (33) :5921-5924