Synthesis of Piperidine Nucleosides as Conformationally Restricted Immucillin Mimics

ABSTRACT: The de novo synthesis of piperidine nucleosides from our homologating agent 5,6-dihydro-1,4-dithiin is herein reported. The structure and conformation of nucleosides were conceived to faithfully resemble the well-known nucleoside drugs Immucillins H and A in their bioactive conformation. NMR analysis of the synthesized compounds confirmed that they adopt an iminosugar conformation bearing the nucleobases and the hydroxyl groups in the appropriate orientation.

SUBMITTER: De Fenza M 

PROVIDER: S-EPMC8001838 | biostudies-literature | 2021 Mar

REPOSITORIES: biostudies-literature