Chemical modification of trehalose. Part XII. Synthesis of azido- and amino-trehaloses via epoxide derivatives

Abstract

2,3-Anhydro-4,6-O-benzylidene-α-D-mannopyranosyl 2,3-anhydro-4,6-O-benzylidene-α-D-mannopyranoside, and the corresponding isomeric allo,allo- and non-symmetrical allo,manno-diepoxides all undergo predominant trans-diaxial ring opening with azide anion to give diazides of altropyranosyl altropyranosides. Likewise, ring opening of the monoepoxide. 2,3-anhydro-4,6-O-benzylidene-α-D-mannopyranosyl 4,6-O-benzylidene-α-D-glucopyranoside gave 3-azido-3-deoxy-α-D-altropyranosyl 4,6-O-benzylidene-α-D-glucopyranoside.