Synthesis of 6-amino-6-deoxy-D-gulono-1,6-lactam and L-gulono-1,6-lactam derived from corresponding 5,6-O-sulfinyl hexono-1,4-lactones

被引：8

作者：

Gireaud, Laurent ^{[1
]}

Chaveriat, Ludovic ^{[1
]}

Stasik, Imane ^{[1
]}

Wadouachi, Anne ^{[1
]}

Beaupere, Daniel ^{[1
]}

机构：

[1] Univ Picardie, Lab Glucides, UMR 6219, F-80039 Amiens, France

来源：

TETRAHEDRON | 2006年 / 62卷 / 31期

关键词：

D-gulono-1,4-lactone; L-gulono-1,4-lactone; 5,6-O-sulfinyl-1,4-lactone; 6-amino-6-deoxy-D-gulonolactam; 6-amino-6-deoxy-L-gulonolactam;

D O I：

10.1016/j.tet.2006.05.017

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Syntheses of 6-amino-6-deoxy-2,3-0-isopropylidene-D-gulono- and L-gulono-1,6-lactams 3 and 4 from corresponding glycono-1,4-lactones are described. Activation of the primary hydroxyl group requires 5,6-cyclic sulfite intermediate to obtain 6-azido-6-deoxy derivatives, which are cyclized after reduction. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：7455 / 7458

页数：4