Total synthesis of the trisaccharide unit of the molecular chaperone down-regulator versipelostatin
Total synthesis of the trisaccharide unit of the molecular chaperone down-regulator versipelostatin
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DOI：
10.1055/s-2006-942450
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发表时间：
2006-07-17
影响因子：
2.6
通讯作者：
Kirschning, Andreas
中科院分区：
文献类型：
--
作者：
Kunst, Eike;Kirschning, Andreas
利用三氟甲磺酸甲酯促进的D-洋地黄毒糖和D-氰马糖的硫代乙基糖基供体与保护的洋地黄毒醛的糖苷化，实现了verspelostatin（grp 78的下调剂）的三糖单元的首次合成。通过制备基于二乙基二硫代膦酸的硫代糖苷来终止合成，所述硫代糖苷准备用于与糖苷配基的进一步糖苷化。两个三氟甲基的NMR光谱数据与versipelostatin报告的数据的比较支持单糖单元以及糖苷键的构型。
The first synthesis of the trisaccharide unit of versipelostatin, a down regulator of grp78, was achieved, utilizing methyl triflate promoted glycosidations of thioethyl glycosyl donors of D-digitoxose and D-cymarose with protected digitoxal. The synthesis was terminated by the preparation of a thioglycoside based on diethyldithionophosphonic acid which is ready for further glycosidations with aglycons. Comparison of NMR spectroscopic data of two trisaccharides with the data reported for versipelostatin supported the configuration of the monosaccharide units as well as glycosidic linkages.