Protecting group free glycosidations using p-toluenesulfonohydrazide donors
Protecting group free glycosidations using p-toluenesulfonohydrazide donors
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DOI：
10.1021/ol801232f
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发表时间：
2008-08-21
期刊：
影响因子：
5.2
通讯作者：
Nitz, Mark
中科院分区：
文献类型：
--
作者：
Gudmundsdottir, Anna V.;Nitz, Mark
引入 N'-吡喃糖基磺酰肼作为糖基供体，用于 O-糖苷、糖基叠氮化物和恶唑啉的无保护基合成。含有还原性末端 N-乙酰葡糖胺残基的单糖和二糖与对甲苯磺酰肼缩合，得到所需的 β-D-吡喃糖供体。这些供体可以用 NBS 激活，然后用所需的醇进行糖苷化或转化为恶唑啉或糖基叠氮化物。
N'-Glycopyranosylsulfonohydrazides are introduced as glycosyl donors for protecting group free synthesis of O-glycosides, glycosyl azides, and oxazolines. Mono- and disaccharides containing a reducing terminal N-acetylglucosamine residue were condensed with P-toluenesulfonylhydrazide to give the desired beta-D-pyranose donors. These donors can be activated with NBS and then glycosidated with the desired alcohol or transformed to the oxazoline or glycosyl azide.