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Published on: August 22, 2018
Synthesis of Piperidine Nucleosides as Conformationally Restricted Immucillin Mimics
Maria De Fenza1, Anna Esposito1, Daniele D'Alonzo1
1Department of Chemical Sciences, University of Naples Federico II, Via Cintia, 80126 Naples, Italy.
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.
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