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Current Medicinal Chemistry

Editor-in-Chief

ISSN (Print): 0929-8673
ISSN (Online): 1875-533X

Chemical Synthesis of Benzamide Riboside

Author(s): K. Krohn, H. Dorner and M. Zukowski

Volume 9 , Issue 7 , 2002

Page: [727 - 731] Pages: 5

DOI: 10.2174/0929867024606876

Price: $65

Abstract

The C-glycosidic nicotinamide riboside analogue (1) was prepared by reaction of ribonolactone 16 with the lithiated 2-oxazoline 13 followed by triethylsilane reduction of the hemiacetal 17 to the tetrahydrofurane 18. Cleavage of the oxazoline group in 20 to the acid 21, conversion of the acid chloride 22 to the amide 23, and hydrogenative debenzylation afforded the benzamide riboside 1. Phosphorylation of the acetonide 26 and acid-catalyzed cleavage of the resulting ketal yielded the pseudonucleotide 27.

Keywords: Synthesis, Benzamide riboside, c-nucleoside, chemical synthesis


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