140363-90-2Relevant academic research and scientific papers
Stereoselective glycosylation of d-galactals by diethyl phosphorochloridite- and AlCl3-assisted Ferrier rearrangement
Chen, Yen-Bo,Wang, Su-I.,Lin, Zi-Ping,Lin, Chun-Hung,Hsieh, Min-Tsang,Lin, Hui-Chang
, p. 350 - 358 (2015/02/18)
α-2,3-Unsaturated galactosides were synthesized in good to excellent yields by the initial activation of d-galactals with diethyl phosphorochloridite and the subsequent glycosyl addition via Ferrier rearrangement with various O-nucleophiles in the presenc
Direct Ferrier rearrangement on unactivated glycals catalyzed by indium(III) chloride
Nagaraj, Paramathevar,Ramesh, Namakkal G.
supporting information; experimental part, p. 3970 - 3973 (2009/10/04)
Anhydrous InCl3 has been shown to efficiently catalyze the Ferrier rearrangement by a direct allylic substitution of the hydroxyl group at C-3 position of glycals to afford the corresponding 2,3-unsaturated glycosides in high yields at ambient
Ferrier Rearrangement under Nonacidic Conditions Based on Iodonium-Induced Rearrangements of Allylic n-Pentenyl Esters, n-Pentenyl Glycosides, and Phenyl Thioglycosides
Lopez, J. Cristobal,Gomez, Ana M.,Valverde, Serafin,Fraser-Reid, Bert
, p. 3851 - 3858 (2007/10/02)
Iodonium-promoted rearrangements of easily accessible allylic n-pentenyl esters, n-pentenyl glycosides, or phenyl thioglycosides result in the generation of the allylic oxocarbenium ion intermediate II of the Ferrier rearrangement, I -> II -> IIIa, of glycals leading to 2,3-unsaturated glycosides.Thus the Ferrier rearranmgement can now be carried out under nonacidic conditions, with NIS or iodonium dicollidinium perchlorate as promoter, to afford good yields of disaccharides in which acid-labile functionalities, either in the glycosyl donor or glycosyl acceptor, have been preserved.
n-Pentenyl Esters Facilitate and Oxidative Alternative to the Ferrier Rearrangement. An Expeditious Route to Sucrose
Lopez, J. Cristobal,Fraser-Reid, Bert
, p. 94 - 96 (2007/10/02)
Ferrier-type reactions can now be carried out under non-acidic conditions by treating 3-n-pentenoyl glycals with iodonium dicollidinium perchlorate whereupon the terminal double bond is chemoselectively activated to furnish an allylic oxo-carbenium ion wh
