Straightforward Synthesis of (1-->2)-Linked Pseudo Aza-C-disaccharides by the Novel Cycloaddition of Enantiopure Cyclic Nitrones to Glycals.
The novel, highly stereoselective, intermolecular cycloaddition reaction of enantiopure cyclic nitrones 8 to 1,2-glycals 9 opens the way to a straightforward synthesis of a broad class of new (1-->2)-linked pseudo aza-C-disaccharides 6, suitable substrates for selective inhibition of glycosidase enzymes. The cycloadditions occur with high stereocontrol, displaying preferential interaction between the bottom face of the glycal and the face of the nitrone anti to the substituent on C-3, with the reagents approaching in an exo fashion. The cycloadditions produced tricyclic isoxazolidines 7 that represent nonreducing pseudo aza-C-disaccharides stable to hydrolytic conditions. The target pseudo aza-disaccharides 6 were obtained by sequential deprotection of the hydroxyl groups and isoxazolidine ring-opening.
Cardona
Francesca
F
Dipartimento di Chimica Organica "Ugo Schiff", Centro di Studio C.N.R. sulla Chimica e la Struttura dei Composti Eterociclici e loro Applicazioni, Università di Firenze, via G. Capponi 9, I-50121, Firenze, Italy, and Institut de Chimie Organique de l'Université de Lausanne, BCH, CG-1015 Lausanne-Dorigny, Switzerland.
Valenza
Silvia
S
Picasso
Sylviane
S
Goti
Andrea
A
Brandi
Alberto
A