14675-52-6Relevant academic research and scientific papers
O- and N-Glycosidation of d-glycals using Ferrier rearrangement under Mitsunobu reaction conditions. Application to N-nucleoside synthesis
Michigami, Kyosuke,Hayashi, Masahiko
experimental part, p. 1092 - 1096 (2012/02/14)
We have disclosed the reaction of 3-hydroxy free glycals with O- or N-nucleophiles under Mitsunobu reaction conditions proceeded to produce 2,3-unsaturated glycosides in good to high yield and moderate stereoselectivity. The reaction would take place via
Scandium triflate catalyzed ferrier rearrangement: An efficient synthesis of 2,3-unsaturated glycopyranosides
Yadav,Reddy,Murthy,Kumar
, p. 1450 - 1451 (2007/10/03)
Scandium(III) trifluoromethanesulfonate is found to catalyze efficiently the O-glycosidation of 3,4,6-tri-O-acetyl-D-glucal with various alcohols and phenols to afford the corresponding 2,3-unsaturated glycosides in excellent yields with good anomeric selectivity.
An easy and efficient preparation of aryl α-O-Δ2-glycosides
Frappa,Sinou
, p. 2941 - 2951 (2007/10/03)
Ferrier reaction between acetylglycals and p-NO2, m-NO2 and p-t-butylphenol after recrystallization gave aryl O-Δ2-glycosides as the pure α anomers. Deacetylation of these compounds and benzylation of the crude diol led to
Reaction of 2,3-unsaturated aryl glycosides with Lewis acids: A convenient entry to C-aryl glycosides
Ramesh,Balasubramanian
, p. 3061 - 3064 (2007/10/02)
A facile synthesis of 2',3'-unsaturated-C-aryl glycosides by BF3 · Et2O mediated 'O' to 'C' transformation of 2,3-unsaturated aryl glycosides is reported.
