Reaction of a lithiated dithiinyl reagent with a O-perbenzylated d-glycono-δ-lactone readily generates the corresponding masked C-vinyl galactosides in high yields and full β-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.
A novel approach to the stereocontrolled synthesis of C-vinyl β-d-galactopyranosides / Romualdo, Caputo; Pasquale, Festa; Guaragna, Annalisa; Palumbo, Giovanni; Pedatella, Silvana. - In: CARBOHYDRATE RESEARCH. - ISSN 0008-6215. - STAMPA. - 338:(2003), pp. 1877-1880. [10.1016/S0008-6215(03)00275-1]
A novel approach to the stereocontrolled synthesis of C-vinyl β-d-galactopyranosides
GUARAGNA, ANNALISA;PALUMBO, GIOVANNI;Silvana Pedatella
2003
Abstract
Reaction of a lithiated dithiinyl reagent with a O-perbenzylated d-glycono-δ-lactone readily generates the corresponding masked C-vinyl galactosides in high yields and full β-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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
