A novel approach to the stereocontrolled synthesis of C-vinyl beta-D-galactopyranosides.
Reaction of a lithiated dithiinyl reagent with a O-perbenzylated D-glycono-delta-lactone readily generates the corresponding masked C-vinyl galactosides in high yields and full beta-selectivity. Removal of the sulfur mask renders the free vinyl aglycone with the vinyl group in either the Z or E configuration, depending on the desulfurization conditions chosen.
Caputo
Romualdo
R
Dipartimento di Chimica Organica e Biochimica, Università di Napoli Federico II, Via Cynthia, 4, 80126 Napoli, Italy.
Festa
Pasquale
P
Guaragna
Annalisa
A
Palumbo
Giovanni
G
Pedatella
Silvana
S
D002236:Carbohydrate Conformation; D005690:Galactose / Q000031:analogs & derivatives* / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000737:chemistry; D008094:Lithium / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D009844:Oligosaccharides / Q000737:chemistry; D000080506:Sialyl Lewis X Antigen; D013237:Stereoisomerism; D013400:Sugar Acids / Q000737:chemistry; D014753:Vinyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D006571:Heterocyclic Compounds; D009844:Oligosaccharides; D000080506:Sialyl Lewis X Antigen; D013400:Sugar Acids; D014753:Vinyl Compounds; C007813:galactonolactone; D008094:Lithium; D005690:Galactose