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23111-00-4 Usage

23111-00-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name Pyridinium, 3-?(aminocarbonyl)?-?1-?β-?D-?ribofuranosyl-?, chloride (1:1)

1.2 Other means of identification

Product number -
Other names -

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:23111-00-4 SDS

23111-00-4Synthetic route

1-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofur-2-yl]-1,4-dihydropyridine-3-carboxamide
19132-12-8

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)
23111-00-4

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)

Conditions
ConditionsYield
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%
C12H17ClN2O6S

C12H17ClN2O6S

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)
23111-00-4

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)

Conditions
ConditionsYield
In methanol at 25℃; Solvent; Temperature;90%
5’,3‘,2’-tri-O-acetyl-1-β-D-ribofuranosylnicotinamide chloride
109527-15-3

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)
23111-00-4

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)

Conditions
ConditionsYield
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%
C18H22NO9(1+)*Cl(1-)

C18H22NO9(1+)*Cl(1-)

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)
23111-00-4

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)

Conditions
ConditionsYield
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
78687-39-5

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)
23111-00-4

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)

Conditions
ConditionsYield
With Amberlite IRA-402 (Cl-Form) In water for 8h;59%
3-carbamoyl-1-(tri-O-benzoyl-β-D-ribofuranosyl)-pyridinium; chloride
122620-02-4

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)
23111-00-4

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)

Conditions
ConditionsYield
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,4R,5R)-3,4-diacetoxy-5-(acetoxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium trifluoromethanesulfonate

3-carbamoyl-1-((2R,3R,4R,5R)-3,4-diacetoxy-5-(acetoxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium trifluoromethanesulfonate

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)
23111-00-4

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)

Conditions
ConditionsYield
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
6974-32-9

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)
23111-00-4

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)

Conditions
ConditionsYield
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
105499-44-3

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)
23111-00-4

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)

Conditions
ConditionsYield
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
98-92-0

nicotinamide

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)
23111-00-4

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)

Conditions
ConditionsYield
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
2,3,5-(tri-O-benzoyl)-D-ribofuranosyl chloride
5991-01-5

2,3,5-(tri-O-benzoyl)-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)
23111-00-4

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetonitrile
2: NH3; methanol
View Scheme
[(2R,5R)-3,4-diacetoxy-5-(3-carbamoyl-4H-pyridin-1-yl)tetrahydrofuran-2-yl]methyl acetate

[(2R,5R)-3,4-diacetoxy-5-(3-carbamoyl-4H-pyridin-1-yl)tetrahydrofuran-2-yl]methyl acetate

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)
23111-00-4

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: methanol; sodium hydroxide / 0.5 h
2: ammonium chloride / water / 1 h / 20 °C
View Scheme
1,2,3,5-tetra-O-acetyl-D-ribofuranose
28708-32-9

1,2,3,5-tetra-O-acetyl-D-ribofuranose

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)
23111-00-4

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)

Conditions
ConditionsYield
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
3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium trifluoromethanesulfonate

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium trifluoromethanesulfonate

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)
23111-00-4

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)

Conditions
ConditionsYield
With sodium chloride; sodium hydroxide In water at 20℃;
With hydrogenchloride In methanol at -8 - 0℃; for 8h; Temperature;16 g
C23H37N2O8Si2(1+)*Cl(1-)

C23H37N2O8Si2(1+)*Cl(1-)

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)
23111-00-4

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)

Conditions
ConditionsYield
With ammonia In methanol at -20℃;
C19H24NO9(1+)*Cl(1-)

C19H24NO9(1+)*Cl(1-)

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)
23111-00-4

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)

Conditions
ConditionsYield
With ammonia In methanol at 0 - 4℃; for 16h;
5’,3‘,2’-tri-O-acetyl-1-β-D-ribofuranosylnicotinamide chloride
109527-15-3

5’,3‘,2’-tri-O-acetyl-1-β-D-ribofuranosylnicotinamide chloride

A

nicotinamide riboside chloride salt
72521-19-8

nicotinamide riboside chloride salt

B

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)
23111-00-4

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)

Conditions
ConditionsYield
With ammonia In methanol at 0℃; for 3h; Inert atmosphere; Overall yield = 0.229 g;A n/a
B n/a
2,3,5-tri-O-acetyl-α-D-ribofuranosyl chloride
105499-44-3

2,3,5-tri-O-acetyl-α-D-ribofuranosyl chloride

trimethylsilyl N-trimethylsilylpyridine-3-carboximidate
102276-96-0

trimethylsilyl N-trimethylsilylpyridine-3-carboximidate

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)
23111-00-4

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1,2-dichloro-ethane / 0 °C
2: ammonia / methanol / -20 °C
View Scheme
nicotinamide
98-92-0

nicotinamide

A

nicotinamide riboside chloride salt
72521-19-8

nicotinamide riboside chloride salt

B

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)
23111-00-4

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1,1,1,3,3,3-hexamethyl-disilazane / 5 h / Reflux
2: calcium carbonate / chloroform / 40.5 h / 0 °C / Inert atmosphere
3: ammonia / methanol / 3 h / 0 °C / Inert atmosphere
View Scheme
[(2R,3R,4R)-3,4-diacetoxy-5-chlorotetrahydrofuran-2-yl]methyl acetate
40554-98-1

[(2R,3R,4R)-3,4-diacetoxy-5-chlorotetrahydrofuran-2-yl]methyl acetate

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)
23111-00-4

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetonitrile / 0.33 h / 70 °C
2: hydrogenchloride / methanol / 12 h / Sealed tube
View Scheme
Multi-step reaction with 2 steps
1: acetonitrile / 50 °C
2: hydrogenchloride / methanol / 12 h / Sealed tube
View Scheme
2,3,5-Tris-O-acetyl-β-D-ribofuranosyl bromide
39925-22-9

2,3,5-Tris-O-acetyl-β-D-ribofuranosyl bromide

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)
23111-00-4

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogen bromide / acetonitrile; acetic acid / 15 h / 0 - 70 °C
2: hydrogen bromide / acetic acid; methanol / 48 h / 5 - 20 °C
3: Amberlite IRA-402 (Cl-Form) / water / 8 h
View Scheme
N1-(2,3,5-Tri-O-acetyl-β-D-ribofuranosyl)-3-aminocarbonylpyridinium bromide
78687-38-4

N1-(2,3,5-Tri-O-acetyl-β-D-ribofuranosyl)-3-aminocarbonylpyridinium bromide

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)
23111-00-4

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogen bromide / acetic acid; methanol / 48 h / 5 - 20 °C
2: Amberlite IRA-402 (Cl-Form) / water / 8 h
View Scheme
1-(β-D-ribofuranosyl)-nicotinamide
1341-23-7

1-(β-D-ribofuranosyl)-nicotinamide

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)
23111-00-4

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)

Conditions
ConditionsYield
With hydrogenchloride; pyrographite In methanol at -10 - -5℃; for 1h; Inert atmosphere;8 g
With hydrogenchloride In methanol at 10 - 15℃; Large scale;9.2 kg
N,N-bis(trimethylsilyl)nicotinamide
69688-12-6

N,N-bis(trimethylsilyl)nicotinamide

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)
23111-00-4

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: tin(IV) chloride / dichloromethane / 1.5 h / 55 °C
1.2: 0.75 h / 0 °C
2.1: methanol; propylamine / 22 h / -5 °C
View Scheme
nicotinamide
98-92-0

nicotinamide

1,2,3,5-tetraacetylribose
13035-61-5

1,2,3,5-tetraacetylribose

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)
23111-00-4

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: boron trifluoride diethyl etherate / dichloromethane / 0.33 h / 5 °C
1.2: 9 h / 5 - 30 °C
2.1: ammonia; methanol / 12 h / -5 - 0 °C / Large scale
View Scheme
1,2,3,5-tetraacetylribose
13035-61-5

1,2,3,5-tetraacetylribose

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)
23111-00-4

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetonitrile / 0.33 h / 20 °C / 760.05 Torr / Molecular sieve; Sealed tube
2: hydrogenchloride / methanol; ethanol / 760.05 Torr / Cooling; Sealed tube
View Scheme
C11H15ClN2O6S

C11H15ClN2O6S

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)
23111-00-4

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)

Conditions
ConditionsYield
In ethanol at 40℃; Solvent; Temperature; Large scale;1.04 kg
3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)
23111-00-4

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)

chlorophosphoric acid diphenyl ester
2524-64-3

chlorophosphoric acid diphenyl ester

C23H24N2O8P(1+)*Cl(1-)

C23H24N2O8P(1+)*Cl(1-)

Conditions
ConditionsYield
With pyridine In acetonitrile at 0 - 5℃; for 12h; Solvent;100%
3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)
23111-00-4

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)

nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

Conditions
ConditionsYield
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 (β-D-nicotinamide riboside)
23111-00-4

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)

2,2-dimethoxy-propane
77-76-9

2,2-dimethoxy-propane

C14H19N2O5(1+)*HO4S(1-)

C14H19N2O5(1+)*HO4S(1-)

Conditions
ConditionsYield
With fuming sulphuric acid In acetonitrile at 0 - 20℃; for 2h; Inert atmosphere;80%
L-Tartaric acid
87-69-4

L-Tartaric acid

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)
23111-00-4

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)

nicotinamide-β-D-ribofuranoside L-hydrogen tartrate

nicotinamide-β-D-ribofuranoside L-hydrogen tartrate

Conditions
ConditionsYield
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 triethylamine under 760.051 Torr; Sealed tube;
Stage #2: L-Tartaric acid With triethylamine In methanol at 0 - 20℃; under 760.051 Torr; pH=4 - 4.5; Sealed tube;
60%
3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)
23111-00-4

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)

1-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofur-2-yl]-1,4-dihydropyridine-3-carboxamide
19132-12-8

1-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofur-2-yl]-1,4-dihydropyridine-3-carboxamide

Conditions
ConditionsYield
With sodium dithionate; sodium hydrogencarbonate at 20℃; for 3h; pH=8.1; Reagent/catalyst; Cooling with ice; Inert atmosphere;55%
mesitaldehyde dimethylacetal
64761-29-1

mesitaldehyde dimethylacetal

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)
23111-00-4

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)

C21H25N2O5(1+)*Cl(1-)

C21H25N2O5(1+)*Cl(1-)

Conditions
ConditionsYield
With CSA In N,N-dimethyl-formamide at 20℃; for 4h;26.6%
3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)
23111-00-4

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)

sodium β-nicotinamide mononucleotide

sodium β-nicotinamide mononucleotide

Conditions
ConditionsYield
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 trichlorophosphate for 1h; Milling;
Stage #2: With sodium hydroxide In water pH=6; Reagent/catalyst;
23%
Multi-step reaction with 3 steps
1: pyridine / acetonitrile / 12 h / 0 - 5 °C
2: platinum(IV) oxide; hydrogen / deuteromethanol / 12 h
3: sodium carbonate / water
View Scheme
3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)
23111-00-4

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)

3-carbamoyl-1-((2R,3R,4S,5R)-5-((((((S)-1-(cyclohexyloxy)-1-oxopropan-2-yl)amino)(phenoxy)phosphoryl)oxy)methyl)-3,4-dihydroxy-tetrahydrofuran-2-yl)pyridin-1-ium chloride

3-carbamoyl-1-((2R,3R,4S,5R)-5-((((((S)-1-(cyclohexyloxy)-1-oxopropan-2-yl)amino)(phenoxy)phosphoryl)oxy)methyl)-3,4-dihydroxy-tetrahydrofuran-2-yl)pyridin-1-ium chloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: CSA / N,N-dimethyl-formamide / 4 h / 20 °C
2.1: tert-butylmagnesium chloride / tetrahydrofuran; 2-methyltetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere
2.2: 3 h / 20 °C / Inert atmosphere
3.1: hydrogenchloride / methanol; water; tetrahydrofuran / 1 h / 20 °C
View Scheme
3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)
23111-00-4

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-((((((S)-1-isopropoxy-1-oxopropan-2-yl)amino)(phenoxy)phosphoryl)oxy)methyl)tetrahydrofuran-2-yl)pyridin-1-ium chloride

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-((((((S)-1-isopropoxy-1-oxopropan-2-yl)amino)(phenoxy)phosphoryl)oxy)methyl)tetrahydrofuran-2-yl)pyridin-1-ium chloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: CSA / N,N-dimethyl-formamide / 4 h / 20 °C
2.1: tert-butylmagnesium chloride / tetrahydrofuran; 2-methyltetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere
2.2: 3 h / 20 °C / Inert atmosphere
3.1: hydrogenchloride / methanol; water; tetrahydrofuran / 1 h / 20 °C
View Scheme
3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)
23111-00-4

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)

C31H37N3O9P(1+)*Cl(1-)

C31H37N3O9P(1+)*Cl(1-)

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: CSA / N,N-dimethyl-formamide / 4 h / 20 °C
2.1: tert-butylmagnesium chloride / tetrahydrofuran; 2-methyltetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere
2.2: 3 h / 20 °C / Inert atmosphere
View Scheme
3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)
23111-00-4

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)

C36H45N3O9P(1+)*Cl(1-)

C36H45N3O9P(1+)*Cl(1-)

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: CSA / N,N-dimethyl-formamide / 4 h / 20 °C
2.1: tert-butylmagnesium chloride / tetrahydrofuran; 2-methyltetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere
2.2: 3 h / 20 °C / Inert atmosphere
View Scheme
3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)
23111-00-4

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)

C33H41N3O9P(1+)*Cl(1-)

C33H41N3O9P(1+)*Cl(1-)

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: CSA / N,N-dimethyl-formamide / 4 h / 20 °C
2.1: tert-butylmagnesium chloride / tetrahydrofuran; 2-methyltetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere
2.2: 3 h / 20 °C / Inert atmosphere
View Scheme
3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)
23111-00-4

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-((((((S)-1-methoxy-1-oxopropan-2-yl)amino)(phenoxy)phosphoryl)oxy)methyl)tetrahydrofuran-2-yl)pyridin-1-ium chloride

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-((((((S)-1-methoxy-1-oxopropan-2-yl)amino)(phenoxy)phosphoryl)oxy)methyl)tetrahydrofuran-2-yl)pyridin-1-ium chloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: CSA / N,N-dimethyl-formamide / 4 h / 20 °C
2.1: tert-butylmagnesium chloride / tetrahydrofuran; 2-methyltetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere
2.2: 3 h / 20 °C / Inert atmosphere
3.1: hydrogenchloride / methanol; water; tetrahydrofuran / 1 h / 20 °C
View Scheme
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