A modular strategy toward the synthesis of heparin-like oligosaccharides using monomeric building blocks in a sequential glycosylation strategy
A modular strategy toward the synthesis of heparin-like oligosaccharides using monomeric building blocks in a sequential glycosylation strategy
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DOI：
10.1021/ja045613g
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发表时间：
2005-03-23
影响因子：
15
通讯作者：
van der Marel, GA
中科院分区：
文献类型：
--
作者：
Codée, JDC;Stubba, B;van der Marel, GA
描述了一种新颖的柔性组装策略用于肝素和硫酸乙酰肝素的模块化合成。报道的策略使用单体构建块来构建寡糖链，以获得最大程度的灵活性。在组装中，使用三氟甲磺酸锍活化剂系统将1-羟基葡糖叠氮基-和1-硫代糖醛酸供体以顺序糖基化方案组合。关键的1-硫代糖醛酸是以有效的方式从双丙酮葡萄糖采用化学和区域选择性氧化的部分保护的葡萄糖和艾杜糖硫代糖苷。
A novel flexible assembly strategy is described for the modular synthesis of heparin and heparan sulfates. The reported strategy uses monomeric building bocks to construct the oligosaccharide chain to attain a maximum degree of flexibility. In the assembly, 1-hydroxyl glucosazido- and 1-thio uronic acid donors are combined in a sequential glycosylation protocol using sulfonium triflate activator systems. The key 1-thio uronic acids were obtained in an efficient manner from diacetone glucose employing a chemo- and regioselective oxidation of partially protected glucose and idose thioglycosides.