Synthesis of 4-octuloses.: Part 7:: Highly stereoselective synthesis of 2,3-anhydrosugar derivatives as key intermediates in the preparation of sugar β-lactams

被引：9

作者：

Izquierdo, I ^{[1
]}

Plaza, MT ^{[1
]}

Robles, R ^{[1
]}

Mota, AJ ^{[1
]}

机构：

[1] Univ Granada, Fac Pharm, Dept Organ Chem, E-18071 Granada, Spain

来源：

TETRAHEDRON-ASYMMETRY | 2000年 / 11卷 / 22期

关键词：

D O I：

10.1016/S0957-4166(00)00421-3

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Reaction of either 1 or 4 with (N,N-dibenzylcarbamoylmethylene)dimethylsulfurane 2 in DMSO afforded 2,3-anhydro-4,5-O-isopropylidene-D-arabino-pentonamide 3 or N,N-dibenzyl 2,3-anhydro-4,5:6,7-di-O-isopropylidene-beta -D-glycero -D-galacto-oct-4-ulo-4,8-pyranosonamide 5, respectively. The configurations of 3 and 5 were determined on the basis of their spectroscopic data, in the first case, and by chemical transformation into the known 2,3-anhydro-4,5:6,7-di-O-isopropylidene-beta -D-glycero-D-galacto-oct-4-ulo-4,8-pyranose 11. Treatment of 3 and 5 with lithium hexamethyldisilazide in THF provided the corresponding sugar beta -lactams 12, 13 and 14, respectively. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：4509 / 4519

页数：11

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