New strategy for the synthesis of 2-(N-substituted-amino)-2-deoxy-D-glucono-1,5-lactone arylsemicarbazones

Abstract

This research focuses on synthesizing selective, and potential inhibitor for O-GlcNAcase (OGA), an enzyme linked to diseases including Alzheimer’s, diabetes and cancer. Based on previous research, this study focuses on the synthesis of 2-(N-substituted-amino)-2-deoxy-D-glucono-1,5-lactone arylsemicarbazones. We have designed and performed a five-step synthesis of 2-(N-2,2,2-trichloroethoxycarbonylamino)-3,4,6-tri-O-acetyl-2-deoxy-D-glucono-1,5-lactone 4-phenylsemicarbazone. After selective cleavage of the Troc group, this compound can be used as a starting material for the preparation of new OGA inhibitors.