Scalable Synthesis of Anomerically Pure Orthogonal-Protected GlcN3 and GalN3 from D-Glucosamine
Scalable Synthesis of Anomerically Pure Orthogonal-Protected GlcN3 and GalN3 from D-Glucosamine
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DOI：
10.1021/acs.orglett.6b02241
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发表时间：
2016-09-02
期刊：
影响因子：
5.2
通讯作者：
Pedersen, Christian Marcus
中科院分区：
文献类型：
--
作者：
Glibstrup, Emil;Pedersen, Christian Marcus
已经开发了从廉价的D-葡糖胺合成正交保护的D-葡糖胺和D-半乳糖胺结构单元的改进的和可规模化的合成。关键反应是一个反转/迁移步骤，提供了一个完全正交的保护基团模式，这是微生物寡糖合成所需的。该方法可以以多克规模进行，因为几个反应可以通过结晶纯化以得到端基异构纯的产物。
An improved and scalable synthesis of orthogonally protected D-glucosamine and D-galactosamine building blocks from inexpensive D-glucosamine has been developed. The key reaction is an inversion/migration step providing access to a fully orthogonal protecting group pattern, which is required for microbial oligosaccharide synthesis. The method can be carried out on a multigram scale as several of the reactions can be purified by crystallization to give anomerically pure products.