Tetrahedron

Syntheses of (3R, 4R, 5R, 6R)-tetrahydroxyazepane (1, 6-dideoxy-1, 6-imino-d-mannitol) and (3S, 4R, 5R, 6R)-tetrahydroxyazepane (1, 6-dideoxy-1, 6-imino-d- …

…, H Regeling, B Zwanenburg, GJF Chittenden

Index: Joseph, Cosam C; Regeling, Henk; Zwanenburg, Binne; Chittenden, Gordon J.F Tetrahedron, 2002 , vol. 58, # 34 p. 6907 - 6911

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Citation Number: 39

Abstract

Syntheses of 1, 6-dideoxy-1, 6-imino-d-mannitol (d-mannoazepane)(1) and 1, 6-dideoxy-1, 6-imino-d-glucitol (d-glucoazepane)(3) from d-isoascorbic acid and d-glucono-1, 5-lactone, respectively, are described. The key step in both routes involved reductive aminative 1, 6- cyclization with retention of configurations to give the corresponding lactams, which were subsequently reduced to afford compounds 1 and 3 in 24 and 28.5%, overall yield, ...