3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)
nicotinamide mononucleotide
Conditions | Yield |
---|---|
With trimethyl phosphite; trichlorophosphate at 0℃; for 12h; Inert atmosphere; | 88.27% |
Stage #1: 3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside) With Sodium trimetaphosphate; sodium hydroxide In water at 30℃; for 4h; pH=9; Stage #2: With hydrogenchloride In water at 10℃; Reagent/catalyst; | 68% |
With nitromethane; water; trichlorophosphate |
3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium bromide
nicotinamide mononucleotide
Conditions | Yield |
---|---|
With trimethyl phosphite; trichlorophosphate at -5 - 0℃; for 7h; | 80% |
With trimethyl phosphite; trichlorophosphate at 0℃; for 4h; | 64% |
nicotinamide mononucleotide
Conditions | Yield |
---|---|
With ammonia In acetonitrile at -5 - 5℃; for 1h; | 80% |
Conditions | Yield |
---|---|
With ethylenediaminetetraacetic acid; ammonium acetate; zirconium(IV) chloride In ethanol at 50℃; for 0.5h; pH 5; | 70% |
With water; zirconium(IV) chloride at 80℃; for 0.5h; Reagent/catalyst; |
nicotinamide mononucleotide
Conditions | Yield |
---|---|
With platinum(IV) oxide; hydrogen In deuteromethanol for 12h; Reagent/catalyst; | 64% |
Conditions | Yield |
---|---|
With trichlorophosphate In tetrahydrofuran at 0 - 20℃; for 12h; | 56% |
3-carbamoyl-1-(2,4-dinitrophenyl)pyridinium chloride
ribose 5-phosphate bis(cyclohexylammonium) salt
nicotinamide mononucleotide
Conditions | Yield |
---|---|
With ammonia 1.) -60 deg C, 36 h; r.t., 1 h; 2.) methanol, ethylene glycol (1:1), 4 deg C, 11 h; | 35% |
nicotinamide
5-phosphoribosyl-1-pyrophosphate
nicotinamide mononucleotide
Conditions | Yield |
---|---|
Enzym aus Erythrocyten; |
3-carbamoyl-1-(2,4-dinitrophenyl)pyridinium chloride
phosphoribosylamine
A
nicotinamide mononucleotide
B
α-nicotinamide mononucleotide
C
2,4-Dinitroanilin
Conditions | Yield |
---|---|
In methanol at 5℃; for 14h; Yield given; | |
In methanol at 5℃; for 14h; |
nicotinamide mononucleotide
Conditions | Yield |
---|---|
enzymatische Spaltung; |
N1-(2,3,5-Tri-O-benzoyl-β-D-ribofuranosyl)-3-aminocarbonylpyridinium bromide
nicotinamide mononucleotide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: NH3 / methanol 2: 80 percent / POCl3, PO(OMe)3 / 7 h / -5 - 0 °C View Scheme | |
Multi-step reaction with 2 steps 1: 55 percent / NH3 / methanol / 72 h / -18 °C 2: 64 percent / Phosphoryl chloride, trimethyl phosphate / 4 h / 0 °C View Scheme |
N1-(2,3,5-Tri-O-acetyl-β-D-ribofuranosyl)-3-aminocarbonylpyridinium bromide
nicotinamide mononucleotide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 80 percent / NH3 / methanol / 20 h / -5 - -3 °C 2: 80 percent / POCl3, PO(OMe)3 / 7 h / -5 - 0 °C View Scheme |
adenosine 5'-monophosphate
nicotinamide mononucleotide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 91 percent / 1.) H(+), H2O / 1.) 100 deg C, 6 min; 2.) 0 deg C 2: 35 percent / NH3 / 1.) -60 deg C, 36 h; r.t., 1 h; 2.) methanol, ethylene glycol (1:1), 4 deg C, 11 h View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: HBr / CH2Cl2 / 3 h / -20 °C 2: liquid sulphur dioxide 3: 55 percent / NH3 / methanol / 72 h / -18 °C 4: 64 percent / Phosphoryl chloride, trimethyl phosphate / 4 h / 0 °C View Scheme | |
Multi-step reaction with 4 steps 1: hydrogen chloride; diethyl ether 2: acetonitrile 3: NH3; methanol 4: POCl3; nitromethane; H2O View Scheme |
2,3,5-tri-O-benzoyl-D-ribofuranosyl bromide
nicotinamide mononucleotide
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: liquid sulphur dioxide 2: 55 percent / NH3 / methanol / 72 h / -18 °C 3: 64 percent / Phosphoryl chloride, trimethyl phosphate / 4 h / 0 °C View Scheme |
2,3,5-tri-O-acetyl-α-D-ribofuranosyl chloride
nicotinamide mononucleotide
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: acetonitrile 2: NH3; methanol 3: POCl3; nitromethane; H2O View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: acetonitrile 2: NH3; methanol 3: POCl3; nitromethane; H2O View Scheme | |
Multi-step reaction with 3 steps 1: trimethylsilyl trifluoromethanesulfonate / tetrahydrofuran / 12 h / 0 - 20 °C 2: sodium ethanolate / ethanol / 1 h / -5 - 5 °C 3: trichlorophosphate / tetrahydrofuran / 12 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: ammonium sulfate / 8 h / 125 °C 2.1: tin(IV) chloride / dichloromethane / 1.5 h / 55 °C 2.2: 0.75 h / 0 °C 3.1: methanol; propylamine / 22 h / -5 °C 4.1: trimethyl phosphite; trichlorophosphate / 12 h / 0 °C / Inert atmosphere View Scheme |
5’,3‘,2’-tri-O-acetyl-1-β-D-ribofuranosylnicotinamide chloride
nicotinamide mononucleotide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: NH3; methanol 2: POCl3; nitromethane; H2O View Scheme | |
Multi-step reaction with 2 steps 1: hydrogenchloride / methanol / 12 h / Sealed tube 2: trichlorophosphate View Scheme |
3-carbamoyl-1-(tri-O-benzoyl-β-D-ribofuranosyl)-pyridinium; chloride
nicotinamide mononucleotide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: NH3; methanol 2: POCl3; nitromethane; H2O View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: acetonitrile 2: NH3; methanol 3: POCl3; nitromethane; H2O View Scheme |
nicotinamide mononucleotide
Conditions | Yield |
---|---|
With trimethyl phosphite; trichlorophosphate at -5 - 0℃; for 12h; Inert atmosphere; |
Conditions | Yield |
---|---|
With nicotinamide phosphoribosyltransferase; tris hydrochloride; ATP; magnesium chloride; D,L-dithiothreitol; bovine serum albumin In water at 37℃; Kinetics; Enzymatic reaction; |
NAD
A
nicotinamide mononucleotide
B
adenosine 5'-diphosphate
C
adenosine
Conditions | Yield |
---|---|
With water; zirconium(IV) oxide at 80℃; for 48h; |
[(2R,3R,4R)-3,4-diacetoxy-5-chlorotetrahydrofuran-2-yl]methyl acetate
nicotinamide mononucleotide
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: acetonitrile / 0.33 h / 70 °C 2: hydrogenchloride / methanol / 12 h / Sealed tube 3: trichlorophosphate View Scheme | |
Multi-step reaction with 3 steps 1: acetonitrile / 50 °C 2: hydrogenchloride / methanol / 12 h / Sealed tube 3: trichlorophosphate View Scheme |
nicotinamide mononucleotide
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: ammonia / methanol / 24 h / -9 - -8 °C 2: hydrogenchloride / methanol / 8 h / -8 - 0 °C 3: trimethyl phosphite; trichlorophosphate / 24 h / -10 - -7 °C View Scheme |
nicotinamide adenine dinucleotide
nicotinamide mononucleotide
Conditions | Yield |
---|---|
With zirconium(IV) chloride In water at 50℃; for 1h; |
Conditions | Yield |
---|---|
With tris(3-hydroxypropyl)phosphine; nicotinamide phosphoribosyltransferase; tris hydrochloride; ATP; magnesium chloride In water at 37℃; pH=7.5; Kinetics; Reagent/catalyst; Enzymatic reaction; |
1,2,3,5-tetraacetylribose
nicotinamide mononucleotide
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: trimethylsilyl trifluoromethanesulfonate / tetrahydrofuran / 12 h / 0 - 20 °C 2.1: ammonia / 1 h / -5 - 5 °C 2.2: 1 h / -5 - 5 °C 3.1: trichlorophosphate / tetrahydrofuran / 12 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: trimethylsilyl trifluoromethanesulfonate / tetrahydrofuran / 12 h / 0 - 20 °C 2: sodium ethanolate / ethanol / 1 h / -5 - 5 °C 3: trichlorophosphate / tetrahydrofuran / 12 h / 0 - 20 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: trimethylsilyl trifluoromethanesulfonate / tetrahydrofuran / 12 h / 0 - 20 °C 2.1: ammonia / 1 h / -5 - 5 °C 2.2: 1 h / -5 - 5 °C 3.1: trichlorophosphate / tetrahydrofuran / 12 h / 0 - 20 °C View Scheme |
Conditions | Yield |
---|---|
In water at 10℃; pH=Ca. 3.8 - 4; | 100% |
Conditions | Yield |
---|---|
In water at 10℃; pH=Ca. 6 - 6.2; | 100% |
Conditions | Yield |
---|---|
In water at 10℃; pH=Ca. 3.9 - 4.4; | 100% |
Conditions | Yield |
---|---|
In water at 10℃; pH=Ca. 3.3 - 3.9; | 100% |
Conditions | Yield |
---|---|
In water at 10℃; pH=Ca. 6 - 6.2; | 100% |
Conditions | Yield |
---|---|
In water pH=2.99 - 3.39; Inert atmosphere; Cooling with ice; | 100% |
Conditions | Yield |
---|---|
In water at 10℃; for 0.166667h; | 97% |
Conditions | Yield |
---|---|
In water pH=3.43 - 4; Cooling with ice; | 96% |
Conditions | Yield |
---|---|
In water pH=3.38 - 3.86; Cooling with ice; | 95% |
Conditions | Yield |
---|---|
In water pH=3.38 - 3.86; Cooling with ice; | 95% |
nicotinamide mononucleotide
adenosine 5'-monophosphate
adenosine‐5'‐triphosphate disodium salt
nicotinamide adenine dinucleotide
Conditions | Yield |
---|---|
With 1,3-dimercaptopropanol; AdK on PAN gel; NAD pyrophosphorylase; PPiase; potassium acetate; magnesium chloride In water for 3h; Ambient temperature; pH: 7.0; | 91% |
Conditions | Yield |
---|---|
In water at 10℃; pH=Ca. 4.4 - 4.6; | 89% |
nicotinamide mononucleotide
Conditions | Yield |
---|---|
With magnesium sulfate; manganese(ll) chloride In formamide at 20℃; for 12h; Inert atmosphere; | 87% |
Conditions | Yield |
---|---|
In water pH=3.22 - 3.9; Inert atmosphere; Cooling with ice; | 85% |
Conditions | Yield |
---|---|
In water pH=3.22 - 3.8; Inert atmosphere; Cooling with ice; | 83% |
nicotinamide mononucleotide
Conditions | Yield |
---|---|
With Saccharomyces cerevisiae inorganic pyrophosphatase; Homo sapiens recombinant nicotinamide mononucleotide adenylyl transferase 1; potassium chloride; sodium chloride; magnesium chloride In ethanol at 37℃; for 2.16667h; Enzymatic reaction; | 81% |
nicotinamide mononucleotide
7-deaza-8-bromo nicotinamide adenine dinucleotide triethylammonium salt
Conditions | Yield |
---|---|
With magnesium sulfate; formamide; manganese(ll) chloride at 20℃; for 48h; | 79% |
Conditions | Yield |
---|---|
In water pH=3.22-3.8; Inert atmosphere; Cooling with ice; | 79% |
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; magnesium chloride; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid at 37℃; | 67% |
Conditions | Yield |
---|---|
In water at 10℃; for 0.166667h; | 67% |
nicotinamide mononucleotide
acetic anhydride
2',3'-di-O-acetylnicotinamide mononucleotide
Conditions | Yield |
---|---|
With pyridine In water at 0℃; for 3h; | 65% |
With pyridine In water at 0℃; for 48h; | |
With pyridine at 0 - 5℃; for 24h; Inert atmosphere; | |
With pyridine In water at -5 - 0℃; for 24h; Inert atmosphere; |
nicotinamide mononucleotide
Conditions | Yield |
---|---|
Stage #1: 6-N-methyladnenosine 5'-monophosphate morpholidated triethylammonium salt; nicotinamide mononucleotide With magnesium sulfate; manganese(ll) chloride In formamide at 20℃; for 48h; Inert atmosphere; Stage #2: With triethylamine carbonate In formamide; acetonitrile | 64% |
C26H36N7O9P
nicotinamide mononucleotide
8-(3-(Boc-aminomethyl)phenyl) NAD
Conditions | Yield |
---|---|
With magnesium sulfate; manganese(ll) chloride In formamide at 20℃; for 24h; Inert atmosphere; | 61% |
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