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Synthesis of β-Nicotinamide Riboside Using an Efficient Two-Step Methodology

Synthesis of β-Nicotinamide Riboside Using an Efficient Two-Step Methodology

Ning Zhang, Anthony A Sauve

Curr Protoc Nucleic Acid Chem. 2017 Dec 24;71:14.14.1-14.14.9.

PMID: 29275540

Abstract:

A two-step chemical method for the synthesis of β-nicotinamide riboside (NR) is described. NR has achieved wide use as an NAD+ precursor (vitamin B3) and can significantly increase central metabolite NAD+ concentrations in mammalian cells. β-NR can be prepared with an efficient two-step procedure. The synthesis is initiated via coupling of commercially available 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose with ethyl nicotinate in the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf). 1 H NMR showed that the product was formed with complete stereoselectivity to produce only the β-isomer in high yield (>90% versus starting sugar). The clean stereochemical result suggests that the coupling proceeds via a cationic cis-1,2-acyloxonium-sugar intermediate, which controls addition by nucleophiles to generate predominantly β-stereochemistry. The subsequent deprotection of esters in methanolic ammonia generates the desired product in 85% overall yield versus sugar. © 2017 by John Wiley & Sons, Inc.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP1105675624	5-Methoxy-N-phenyl-4-(trimethylsilyl)nicotinamide		1105675-62-4	Price

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