F. Sarabiagarcia et Fj. Lopezherrera, STUDIES ON THE SYNTHESIS OF TUNICAMYCIN - THE PREPARATION OF 7-DEOXY-2-DEAMINO-6-HYDROXY TUNICAMINE AND RELATED PRODUCTS, Tetrahedron, 52(13), 1996, pp. 4757-4768
The condensation of methyl 5-diazo-2,3-O-isopropylidene-beta-D-ribofur
anoside with :3,4-di-O-isopropylidene-D-galactohexonodialdo-1,5 pyrano
side gave the ketone C-disaccharide 11 as the sole product. This keton
e was transformed into different derivatives. Thus, its reduction led
stereoselectively to the corresponding alcohols. Similar transformatio
ns]ed to the corresponding alkane and amino derivatives, of potential
biological interest as inhibitors for glycosidases. These results can
be useful for the synthesis of tunicamine and its analogues.