PubMed:35643049 JSONTXT 14 Projects

Oxocarbenium ion cyclizations for the synthesis of disaccharide mimetics of 2-amino-2-deoxy-pyranosides: Application to the carbasugar of β-galactosamine-(1,4)-3-O-methyl-D-chiro-inositol. The synthesis of the carbasugar of β-galactosamine-(1,4)-3-O-methyl-D-chiro-inositol (INS-2), a potential tool for studying glucose metabolism, is described. The synthetic strategy, entails an oxocarbenium ion cyclization on a chiro-inositol derived, thioacetal-enol ether to give a carbocyclic enol ether, which is elaborated to the 2-amino-2-deoxy carbasugar framework via a 2-oximo derivative.