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2-乙酰氨基-2-脱氧糖的选择性新戊酰化反应。

Selective pivaloylation of 2-acetamido-2-deoxy sugars.

作者信息

Ljevaković D, Tomić S, Tomasić J

机构信息

Department of Radioimmunology, Institute of Immunology, Zagreb, Yugoslavia.

出版信息

Carbohydr Res. 1988 Nov 1;182(2):197-205. doi: 10.1016/0008-6215(88)84003-5.

DOI:10.1016/0008-6215(88)84003-5
PMID:3242804
Abstract

Selective pivaloylation of 2-acetamido-2-deoxy-D-glucose, its methyl alpha- and beta-glycosides, and the methyl alpha-glycoside of N-acetyl-D-muramic acid under various conditions has been studied. The structures of the products were established by 1H-n.m.r. spectroscopy and acetylation. The orders of acylation, HO-6 greater than HO-3 greater than HO-1 greater than HO-4 for 2-acetamido-2-deoxy-D-glucose and HO-6 greater than HO-3 greater than HO-4 for its methyl glycosides, were established. Methyl 2-acetamido-2-deoxy-3,6-di-O-pivaloyl-alpha- and -beta-D-glucopyranosides and 2-acetamido-2-deoxy-1,3,4,6-tetra-O-pivaloyl-D-glucopyranose were hydrolysed by rabbit serum esterases.

摘要

研究了在各种条件下对2-乙酰氨基-2-脱氧-D-葡萄糖、其α-和β-甲基糖苷以及N-乙酰-D-胞壁酸的α-甲基糖苷进行选择性新戊酰化反应。通过¹H-核磁共振光谱和乙酰化反应确定了产物的结构。确定了酰化顺序，对于2-乙酰氨基-2-脱氧-D-葡萄糖，HO-6＞HO-3＞HO-1＞HO-4，对于其甲基糖苷，HO-6＞HO-3＞HO-4。2-乙酰氨基-2-脱氧-3,6-二-O-新戊酰基-α-和-β-D-吡喃葡萄糖苷以及2-乙酰氨基-2-脱氧-1,3,4,6-四-O-新戊酰基-D-吡喃葡萄糖可被兔血清酯酶水解。

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