140363-91-3

Upstream product

• 140460-23-7 4,6-Di-O-benzyl-3-O-(4-pentenoyl)-D-gulal 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 140363-86-6 4,6-Di-O-benzyl-3-O-(4-pentenoyl)-D-galactal 
• 81928-98-5 4,6-di-O-benzyl-D-galactal 
• 591-80-0 pent-4-enoic acid 

Relevant academic research and scientific papers

Ferrier Rearrangement under Nonacidic Conditions Based on Iodonium-Induced Rearrangements of Allylic n-Pentenyl Esters, n-Pentenyl Glycosides, and Phenyl Thioglycosides

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

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