Studies on the synthesis of tunicamycin. The preparation of 7-deoxy-2-deamino-6-hydroxy tunicamine and related products

Article abstract of DOI:10.1016/0040-4020(96)00146-9

The condensation of methyl 5-deoxy-5-diazo-2,3-O-isopropylidene-β-D-ribofuranoside with 1,2:3,4-di-O-isopropylidene-D-galactohexonodialdo-1,5-pyranoside gave the ketone C-disaccharide 11 as the sole product. This ketone was transformed into different derivatives. Thus, its reduction led stereoselectively to the corresponding alcohols. Similar transformations led 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.