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| CAS No.: | 23111-00-4 |
|---|---|
| Name: | Nicotinamide riboside chloride |
| Molecular Structure: | |
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| Formula: | C11H15ClN2O5 |
| Molecular Weight: | 290.703 |
| Synonyms: | Nicotinamide riboside chloride;3-Carbamoyl-1-beta-D-ribofuranosylpyridinium chloride |
| EINECS: | 200-184-4 |
| PSA: | 116.89000 |
| LogP: | -4.61120 |
1-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofur-2-yl]-1,4-dihydropyridine-3-carboxamide
3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)
| Conditions | Yield |
|---|---|
| With ammonium chloride In water at 20℃; for 1h; Solvent; | 100% |
| With 5%-palladium/activated carbon; ammonium chloride In isopropyl alcohol at 20℃; under 1500.15 Torr; for 20h; Reagent/catalyst; Temperature; Solvent; Pressure; Green chemistry; | 89% |
3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)
| Conditions | Yield |
|---|---|
| In methanol at 25℃; Solvent; Temperature; | 90% |
5’,3‘,2’-tri-O-acetyl-1-β-D-ribofuranosylnicotinamide chloride
3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)
| Conditions | Yield |
|---|---|
| With ammonia In methanol at -15 - -10℃; Temperature; Reagent/catalyst; | 82% |
| With ethanol; ammonia at 10 - 20℃; for 3h; | 78% |
| With methanol; ammonia at -5 - 0℃; for 12h; Large scale; | 78% |
3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)
| Conditions | Yield |
|---|---|
| With methanol; ammonia at 0℃; for 24h; Large scale; | 67% |
3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium bromide
3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)
| Conditions | Yield |
|---|---|
| With Amberlite IRA-402 (Cl-Form) In water for 8h; | 59% |
3-carbamoyl-1-(tri-O-benzoyl-β-D-ribofuranosyl)-pyridinium; chloride
3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)
| Conditions | Yield |
|---|---|
| With sodium methylate In methanol at -5℃; for 24h; | 52.6% |
| With methanol; ammonia | |
| With ammonia In methanol at -32℃; for 120h; | 0.28 g |
3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)
| Conditions | Yield |
|---|---|
| With hydrogenchloride In methanol; ethanol under 760.051 Torr; Cooling; Sealed tube; | 2% |
| Multi-step reaction with 3 steps 1: sodium hydrogencarbonate; sodium dithionite / water / 0.33 h / Inert atmosphere 2: methanol; sodium hydroxide / 0.5 h 3: ammonium chloride / water / 1 h / 20 °C View Scheme | |
| Multi-step reaction with 2 steps 1: ammonia / methanol / 24 h / -9 - -8 °C 2: hydrogenchloride / methanol / 8 h / -8 - 0 °C View Scheme |
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose
3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1: hydrogen chloride; diethyl ether 2: acetonitrile 3: NH3; methanol View Scheme |
2,3,5-tri-O-acetyl-α-D-ribofuranosyl chloride
3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: acetonitrile 2: NH3; methanol View Scheme | |
| Multi-step reaction with 2 steps 1: 1,2-dichloro-ethane / 0 °C 2: ammonia / methanol / 16 h / 0 - 4 °C View Scheme |
nicotinamide
3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: acetonitrile 2: NH3; methanol View Scheme | |
| Multi-step reaction with 4 steps 1.1: 1,1,1,3,3,3-hexamethyl-disilazane / 130 °C 1.2: 0.5 h 2.1: sodium hydrogencarbonate; sodium dithionite / water / 0.33 h / Inert atmosphere 3.1: methanol; sodium hydroxide / 0.5 h 4.1: ammonium chloride / water / 1 h / 20 °C View Scheme | |
| Multi-step reaction with 3 steps 1.1: acetonitrile 1.2: 0.5 h / 20 °C 2.1: methanol; sodium methylate / 0.5 h / 3 - 5 °C 3.1: sodium hydroxide; sodium chloride / water / 20 °C View Scheme |
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