Bicyclic azasugars containing a glycosidic heteroatom 2: D-lyxose analogues

被引：9

作者：

Berges, DA ^{[1
]}

Zhang, N ^{[1
]}

Hong, LW ^{[1
]}

机构：

[1] Brigham Young Univ, Dept Chem & Biochem, Provo, UT 84602 USA

来源：

TETRAHEDRON | 1999年 / 55卷 / 50期

关键词：

carbohydrate mimetics; aza compounds; enzyme inhibitors; conformation;

D O I：

10.1016/S0040-4020(99)00901-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Bicyclic azasugar analogues of D-lyxose containing a glycosidic heteroatom that is O, N, or S have been prepared from 5-O-tosyl-D-lyxose and characterized by NMR spectroscopy. The nitrogen analogue has an overwhelming preference to be the beta-anomer, but the oxygen and sulfur compounds exist as mixtures of anomers with the alpha-anomer predominating in the latter case. The alpha-anomers undergo conformational equilibration with the sulfur analogue being fast at room temperature but the oxygen compound requiring 60 degrees C to achieve fast exchange and a sharply resolved H-1 NMR spectrum at 500 MHz. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：14251 / 14260

页数：10

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