Anomeric reactivity-based one-pot synthesis of heparin-like oligosaccharides
Anomeric reactivity-based one-pot synthesis of heparin-like oligosaccharides
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DOI：
10.1021/ja073098r
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发表时间：
2007-10-24
影响因子：
15
通讯作者：
Wong, Chi-Huey
中科院分区：
文献类型：
--
作者：
Polat, Tuelay;Wong, Chi-Huey
一种高效的一锅法，用于合成肝素和硫酸乙酰肝素低聚糖利用硫代糖苷具有明确的反应性作为积木描述。由于糖醛酸在一锅法合成中作为糖基供体的反应性低，因此使用L-吡喃葡萄糖基和D-吡喃葡萄糖基硫代糖苷5和10作为供体。糖醛酸的形成通过在C-6的选择性氧化后进行的低聚糖的组装。在二糖17、18、四糖23和五糖26的代表性合成中证明了这种具有硫酸根掺入灵活性的可编程策略的效率。
A highly efficient one-pot methodology is described for the synthesis of heparin and heparan sulfate oligosaccharides utilizing thioglycosides with well-defined reactivity as building blocks. L-ldopyranosyl and D-glucopyranosyl thioglycosides 5 and 10 were used as donors due to low reactivity of uronic acids as the glycosyl donors in the one-pot synthesis. The formation of uronic acids by a selective oxidation at C-6 was performed after assembly of the oligosaccharides. The efficiency of this programmable strategy with the flexibility for sulfate incorporation was demonstrated in the representative synthesis of disaccharides 17, 18, tetrasaccharide 23, and pentasaccharide 26.