Dipartimento di Scienze del Farmaco, Università del Piemonte Orientale A. Avogadro , L.go Donegani, 2-28100 Novara, Italy.
Org Lett. 2014 Feb 7;16(3):952-5. doi: 10.1021/ol403688t. Epub 2014 Jan 15.
A convenient, simple, and high-yielding five-step synthesis of a sphingosine acceptor from phytosphingosine is reported, and its behavior in glycosylation reactions is described. Different synthetic paths to sphingosine acceptors using tetrachlorophthalimide as a protecting group for the sphingosine amino function and different glycosylation methods have been explored. Among the acceptors tested, the easiest accessible acceptor, unprotected on the two hydroxyl groups in positions 1 and 3, was regioselectively glycosylated on the primary position, the regioselectivity depending on the donor used.
从植物鞘氨醇出发，报道了一种方便、简单、高产的神经酰胺受体五步法合成方法，并描述了其在糖苷化反应中的行为。使用四氯邻苯二甲酰亚胺作为神经酰胺氨基官能团的保护基，探索了不同的合成神经酰胺受体的路线和不同的糖苷化方法。在所测试的受体中，最容易获得的受体在 1 位和 3 位的两个羟基上没有保护，在主位上优先进行区域选择性糖苷化，区域选择性取决于所用供体。
