Synthesis of Piperidine Nucleosides as Conformationally Restricted Immucillin Mimics
2021
Maria De Fenza | Anna Esposito | Daniele D’Alonzo | Annalisa Guaragna
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.
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