Improved synthesis of 6-amino-6-deoxy-D-galactono-1,6-lactam and D-mannono-1,6-lactam from corresponding unprotected D-hexono-1,4-lactones

被引：13

作者：

Chaveriat, L ^{[1
]}

Stasik, I ^{[1
]}

Demailly, G ^{[1
]}

Beaupère, D ^{[1
]}

机构：

[1] Univ Picardie, Lab Glucides, F-80039 Amiens, France

来源：

TETRAHEDRON | 2004年 / 60卷 / 09期

关键词：

D-galactono-1,4-lactone; D-mannono-1,4-lactone; 6-bromo-6-deoxy-D-hexono-1,4-lactones; seven-member azasugars; 6-amino-6-deoxy-D-galactono; D-mannono-1,6-lactams;

D O I：

10.1016/j.tet.2003.12.062

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Regioselective bromination of unprotected D-galactono-1,4-lactone and D-mannono-1,4-lactone with PPh3/CBr4 led to 6-bromo-6-deoxy derivatives. These intermediates were treated with LiN3 and hydrogenated to give 6-amino-6-deoxy-D-galactono-1,6-lactam (8) and 6-amino-6-deoxy-D-mannono-1,6-lactam (13) in 74 and 67% overall yield, respectively. (C) 2004 Elsevier Ltd. All rights reserved.

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页码：2079 / 2081

页数：3

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