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n-Pentenyl esters facilitate an oxidative alternative to the Ferrier rearrangement. An expeditious route to sucrose

1992; Royal Society of Chemistry; Issue: 2 Linguagem: Inglês

10.1039/c39920000094

2050-5639

J. Cristóbal López, Bert Fraser‐Reid,

Glycosylation and Glycoproteins Research

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 which reacts at the anomeric position with monosaccharide alcohols to afford 2,3-unsaturated disaccharides in fairly good yields.