Jayaprakash K N, Fraser-Reid Bert
Natural Products and Glycotechnology Research Institute, Inc., 4118 Swarthmore Road, Durham, North Carolina 27707, USA.
Org Lett. 2004 Nov 11;6(23):4211-4. doi: 10.1021/ol0483697.
Nuanced activation of n-pentenyl, thioglycoside, and trichloroacetimidate donors by lanthanide salts coupled with donor/acceptor matching can simplify oligosaccharide assembly. Thus, a one-pot, double-differential glycosidation process can be designed, in which an n-pentenyl acceptor-diol is chemo- and regioselectively glycosidated by using an n-pentenyl ortho ester under the agency of Yb(OTf)(3)/NIS followed by in situ addition of a 2-O-acylated trichloroacetimidate or ethyl thioglycoside to effect stereoselective glycosidation at the remaining OH.
镧系盐对正戊烯基、硫代糖苷和三氯乙酰亚胺酯供体的细微活化作用，再结合供体/受体匹配，可简化寡糖组装。因此，可以设计一种一锅双差向糖苷化过程，其中在Yb(OTf)₃/NIS作用下，使用正戊烯基原酸酯对正戊烯基受体二醇进行化学和区域选择性糖苷化，然后原位添加2-O-酰化三氯乙酰亚胺酯或乙基硫代糖苷，以在剩余的羟基上实现立体选择性糖苷化。
