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2 article(s) from Migaud, Marie E

Syntheses and chemical properties of β-nicotinamide riboside and its analogues and derivatives

Mikhail V. Makarov and
Marie E. Migaud

Beilstein J. Org. Chem. 2019, 15, 401–430, doi:10.3762/bjoc.15.36

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Graphical Abstract

Figure 1: Structural formulas of Nam, NA, NR⁺, NMN, and NAD⁺.

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Figure 2: Main synthetic routes to nicotinamide riboside (NR⁺X⁻).

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Scheme 1: Synthesis of NR⁺Cl⁻ based on the reaction of peracylated chlorosugars with Nam.

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Figure 3: Predominant formation of β-anomer over α-anomer of NR⁺X⁻.

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Scheme 2: Synthesis of NR⁺Cl⁻ by reacting 3,5-di-O-benzoyl-D-ribofuranosyl chloride (5) with Nam (1a).

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Figure 4: Mechanism of the formation of the β-anomer of the glycosylated product in the case of the reaction ...

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Scheme 3: Synthesis of NR⁺Br⁻ by reacting bromosugars with Nam (1a).

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Scheme 4: Synthesis of NR⁺OTf⁻ based on the glycosylation of Nam (1a) with tetra-O-acetyl-β-D-ribofuranose (2a...

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Scheme 5: Improved synthesis of NR⁺OTfˉ and NAR⁺OTfˉ based on the glycosylation of pre-silylated Nam or NA wi...

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Scheme 6: Synthesis of triacetylated NAR⁺OTf⁻ by glycosylation of nicotinic acid trimethylsilyl ester with te...

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Scheme 7: Synthesis of NR⁺Cl⁻ from NR⁺OTf⁻ by means of ion exchange with sodium chloride solution.

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Scheme 8: Synthesis of acylated NR⁺OTf⁻ by means of ion exchange with sodium chloride.

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Scheme 9: Synthesis of triacetylated derivatives of NAR⁺ by glycosylation of nicotinic acid esters with ribos...

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Scheme 10: Synthesis of NR⁺OTf⁻ from the triflate salt of ethyl nicotinate-2,3,5-triacetyl-β-D-riboside in met...

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Scheme 11: Reaction of 2,3,5-tri-O-acetyl-β-phenyl nicotinate riboside triflate salt with secondary and tertia...

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Scheme 12: Synthesis of NMN based on the Zincke reaction of N-(2,4-dinitrophenyl)-3-carbamoylpyridinium chlori...

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Scheme 13: Synthesis of NMN based on the Zincke reaction of N-(2,4-dinitrophenyl)-3-carbamoylpyridinium chlori...

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Scheme 14: Efficacious protection of 2′,3′-hydroxy groups of NR⁺X⁻.

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Scheme 15: Protection of the 2′,3′-hydroxy groups of NR⁺Cl^– with a mesitylmethylene acetal group.

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Figure 5: Reduction of derivatives of NR⁺Xˉ into corresponding 1,2-; 1,4-; 1,6-NRH derivatives.

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Figure 6: Mechanism of the reduction of the pyridinium core with dithionite as adapted from [67].

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Scheme 16: Reduction of triacylated NR⁺OTf^– derivatives by sodium dithionite followed by complete removal of a...

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Figure 7: Structural formulas of iridium and rhodium catalysts (a)–(d) for regeneration of NAD(P)H from NAD(P)...

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Figure 8: Two approaches to synthesis of 5′-derivatives of NR⁺.

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Scheme 17: Synthesis of NMN starting from NR⁺ salt.

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Scheme 18: Efficient synthesis of NMN by phosphorylation of 2′,3′-O-isopropylidene-NR⁺ triflate followed by re...

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Scheme 19: Synthesis of a bisphosphonate analogue of β-NAD⁺ based on DCC-induced conjugation of 2′,3′-O-isopro...

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Scheme 20: Synthesis of 5′-acyl and 2′,3′,5′-triacyl derivatives of NR⁺.

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Figure 9: Structural formulas of NMN analogues 39–41.

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Scheme 21: Synthesis of 5′-phosphorylated derivatives of NR⁺ using a “reduction–modification–oxidation” approa...

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Scheme 22: Synthesis of 5′-phosphorylated derivatives of NR⁺ using a “reduction–modification–reoxidation” appr...

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Figure 10: Structural formulas of 5′-phosphorylated derivatives of NR⁺.

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Scheme 23: Synthesis of 5′-phosphorylated derivatives of NR⁺ using a direct NR⁺ phosphorylation approach.

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Figure 11: Structural formulas of amino acid NR⁺ conjugates.

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Scheme 24: Synthesis of amino acid NR⁺ conjugates using NRH and protected amino acid under CDI-coupling condit...

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Figure 12: Chemical structures of known isotopically labelled NR⁺ analogues and derivatives.

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Scheme 25: Synthesis of [2′-³H]-NR⁺ and [2′-³H]-NMN.

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Scheme 26: Synthesis of α- and β-anomers of [1′-²H]-NMN.

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Review

Published 13 Feb 2019

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Solvent- controlled regioselective protection of allyl- 4,6-benzylidene glucopyranosides

Kerry Ann Ness and
Marie E. Migaud

Beilstein J. Org. Chem. 2007, 3, No. 26, doi:10.1186/1860-5397-3-26

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Scheme 1: Target partially protected sugar 1.

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Scheme 2: Selective C-2 benzylation and confirmation of the regiochemistry through acetylation of the C-3 hyd...

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Published 26 Sep 2007

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