A facile stereoselective synthesis of alpha-glycosyl ureas.
Alpha-glycosyl ureas can be synthesised directly from tetra-O-benzyl glycosyl azides and isocyanates, using a one-pot procedure that is simple and general in scope. The benzyl protecting groups are easily removed from the urea products by catalytic hydrogenation. The synthesised alpha-glycosyl ureas represent a new class of neo-glycoconjugates with the potential of being resistant towards carbohydrate processing enzymes.
Bianchi
Aldo
A
Dipartimento di Chimica Organica e Industriale, Università degli Studi di Milano, via Venezian 21, 20133 Milano, Italy.
Ferrario
Davide
D
Bernardi
Anna
A
D001386:Azides / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis*; D017953:Isocyanates / Q000737:chemistry; D013237:Stereoisomerism; D014508:Urea / Q000031:analogs & derivatives* / Q000138:chemical synthesis*
D001386:Azides; D006027:Glycosides; D017953:Isocyanates; D014508:Urea