A simplified Ramberg-Backlund approach to novel C-glycosides and C-linked disaccharides
A simplified Ramberg-Backlund approach to novel C-glycosides and C-linked disaccharides
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DOI：
10.1002/anie.200390356
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发表时间：
2003-01-01
影响因子：
16.6
通讯作者：
Taylor, RJK
中科院分区：
文献类型：
--
作者：
McAllister, GD;Paterson, DE;Taylor, RJK
一系列受保护的呋喃酶与膦酸盐（II）依次进行Horner-Wadsworth-Emmons (HWE)/共轭加成/ Ramberg-Baecklund反应（RBR），得到相应的(E)-2-苯乙烯基c -苷。在这些条件下，观察到异构体位置的外聚现象。该序列的一罐变体被用于提供c -糖苷（VIII）的优良产量。单糖衍生膦酸盐（IX）也可以用于该方法，从而得到烯基双糖（XI）。双膦酸盐（XII）提供了新的c链双呋喃糖双糖（XV）。
A range of protected furanoses undergo a Horner—Wadsworth—Emmons (HWE)/conjugate-addition/Ramberg—Baecklund Reaction (RBR) sequence with phosphonate (II) to give the corresponding (E)-2-styrenyl C-glycosides. Epimerization at the anomeric position under these conditions is observed. A one pot variant of this sequence is performed to afford C-glycoside (VIII) in excellent yield. Monosaccharide derived phosphonate (IX) can be also employed for this method leading to alkenyl disaccharide (XI). Bisphosphonate (XII) gives access to the novel C-linked bisfuranose disaccharide (XV).