TY  - BOOK
AU  - Hadd,M.J.
AU  - Gervay,J.
TI  - Glycosyl iodides are highly efficient donors under neutral conditions
KW  - GLYCOSYL IODIDE
KW  - GLYCOSYL BROMIDE
KW  - A-GLYCOSYLATION
KW  - IN SITU ANOMERIZATION
KW  - HALIDE-CATALYZED ANOMERIZATION
KW  - TREHALOSE ANALOGS
N2  - Glycosyl iodides have been prepared and subjected to glycosylation under neutral conditions. The reactions are highly efficient, giving a glycosides even with sterically demanding glycosyl acceptors. Glucosyl iodides react with allyl alcohol slowest and require refluxing conditions. Galactosyl iodides are intermediate in reactivity, providing the allyl glycoside in 3 h at room temperature, whereas glycosylation of fucosyl iodides occurs in less than 1 h under similar conditions. The scope and limitations of the reactions were demonstrated with a variety of acceptors, including an anomeric hydroxyl group, to give trehalose analogs. b-Selective glycosylation of glucosyl iodides, in the absence of C-2 participation, could be achieved by simply changing the solvent from benzene to acetonitrile
UR  - https://drive.google.com/file/d/1a7qM6nJcznMS163JXKGSNvztyC3UoJO3/view?usp=drivesdk
ER  -