Chemical Synthesis of Benzamide Riboside

K.      Krohn; H.      Dorner; M.      Zukowski

doi:10.2174/0929867024606876

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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Current Medicinal Chemistry

Title: Chemical Synthesis of Benzamide Riboside

Volume: 9 Issue: 7

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

Affiliation:

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

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.

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Krohn K., Dorner H. and Zukowski M., Chemical Synthesis of Benzamide Riboside, Current Medicinal Chemistry 2002; 9 (7) . https://dx.doi.org/10.2174/0929867024606876