Reductive Dephthalimidation: A Mild and Efficient Method for The N-Phthaumido Deprotection During Ougosaccharide Synthesis
Reductive Dephthalimidation: A Mild and Efficient Method for The N-Phthaumido Deprotection During Ougosaccharide Synthesis
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还原脱邻苯二甲酰亚胺化：一种温和有效的寡糖合成过程中 N-邻苯二甲酰氨基脱保护方法
DOI：
10.1080/07328308808057560
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发表时间：
1988
影响因子：
1
通讯作者：
P. Garegg
中科院分区：
文献类型：
--
作者：
F. Dasgupta;P. Garegg
摘要具有生物活性的寡糖、半抗原及其蛋白结合物的合成是一个重要的研究领域，因为它们在抗原-抗体相互作用和受体效应中起着重要作用。其中许多分子含有α或β连接的2-乙酰氨基-2-脱氧-D-氨基葡萄糖(GlcNAc)部分。最常见的是，在低聚糖的合成过程中，引入β-糖基连接的GlcNAc残基是通过恶唑啉2或邻苯二甲酰亚胺法3实现的。在这些化合物中，后者是首选的，因为在C-1上具有卤素或硫代烷基团的2-N-邻苯二甲酰亚胺保护的糖胺单元一直被证明是比恶唑啉更有效的供体。然而，一次又一次地证明，通过肼分解将N-邻苯二甲酰亚胺转化为胺是不够的。这往往导致在其他有效的合成后，总收率较低。最近的研究表明，在温和的条件下，可以从一些氨基酸4中去除邻苯二甲酰亚胺的功能。什么..。
Abstract Synthesis of biologically active oligosaccharides, haptens and their protein conjugates is a major area of interest because of their role in antigen-antibody interaction and receptor effects1. A number of these molecules contain α-or β-linked 2-acetamido-2-deoxy-D-glucosamine (GlcNAc) moieties. Most commonly, during the oligosaccharide synthesis, introduction of the β-glycosidically linked GlcNAc residue is achieved by either the oxazoline2 or the phthalimido method3. Of these, the latter is preferred because 2-N-phthalimido protected glycosamine units having a halogen or a thioalkyl group at C-1 have consistently proved to be more efficient donors than are the oxazolines. However, time and again, subsequent conversion of the N-phthalimido to amine by hydrazinolysis has proved inadequate. This has often resulted in a poor overall yield after an otherwise efficient synthesis. Recently it was shown that the phthalimido function could be removed under mild conditions from a number of amino acids4. W...