151265-18-8Relevant articles and documents
Stereoselective Phenylselenoglycosylation of Glycals Bearing a Fused Carbonate Moiety toward the Synthesis of 2-Deoxy-β-galactosides and β-Mannosides
Li, Zhongjun,Meng, Shuai,Yao, Wang,Zhong, Wenhe
, (2020/04/09)
A phenylselenoglycosylation reaction of glycal derivatives mediated by diphenyl diselenide and phenyliodine(III) bis(trifluoroacetate) under mild conditions is described. Stereoselective glycosylation has been achieved by installing fused carbonate on those glycals. 3,4-O-Carbonate galactals and 2,3-O-carbonate 2-hydroxyglucals are converted into corresponding glycosides in good yields with excellent β-selectivity, resulting in 2-phenylseleno-2-deoxy-β-galactosides and 2-phenylseleno-β-mannosides which are good precursors of 2-deoxy-β-galactosides and β-mannosides, respectively.
An Unexpected Sialylation: Total Syntheses of GM4 and a Positional Isomer
Gervay, Jacquelyn,Peterson, John M.,Oriyama, Takeshi,Danishefsky, Samuel J.
, p. 5465 - 5468 (2007/10/02)
The use of glycals 3 and 4 as precursors to 1,2-ahhydrosugars greatly simplifies the installation of a β-linked ceramide glycoside.By permuting the introduction of the ceramide and the sialic acid, one can access the ganglioside GM4 (1) and, by an unexpected regioselective glycosylation, its NeuAc (2->2) Gal positional isomer 10.
