Product Name

  • Name

    (R)-(+)-9-(2-Hydroxypropyl)adenine

  • EINECS 604-188-0
  • CAS No. 14047-28-0
  • Article Data37
  • CAS DataBase
  • Density 1.57 g/cm3
  • Solubility
  • Melting Point 193 °C
  • Formula C8H11N5O
  • Boiling Point 457.7 °C at 760 mmHg
  • Molecular Weight 193.208
  • Flash Point 230.6 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 14047-28-0 ((R)-(+)-9-(2-Hydroxypropyl)adenine)
  • Hazard Symbols
  • Synonyms 9H-Purine-9-ethanol,6-amino-a-methyl-, (R)-;9H-Purine-9-ethanol, 6-amino-a-methyl-, D- (8CI);(R)-9-(2-Hydroxypropyl)adenine;9-[(2R)-2-Hydroxypropyl]adenine;D-(-)-9-(2-Hydroxypropyl)adenine;
  • PSA 89.85000
  • LogP 0.37050

Synthetic route

(R)-6-acetyl-9-(2-hydroxypropyl)adenine

(R)-6-acetyl-9-(2-hydroxypropyl)adenine

(R)-9-(2-hydroxypropyl)adenine
14047-28-0

(R)-9-(2-hydroxypropyl)adenine

Conditions
ConditionsYield
With sodium hydroxide In water at 93℃; for 2h; Temperature;97.7%
(R)-1-(6-chloro-9H-purin-9-yl) propan-2-ol
180587-74-0

(R)-1-(6-chloro-9H-purin-9-yl) propan-2-ol

(R)-9-(2-hydroxypropyl)adenine
14047-28-0

(R)-9-(2-hydroxypropyl)adenine

Conditions
ConditionsYield
With ammonium hydroxide In 1,4-dioxane at 100 - 110℃; Sealed tube; Large scale;96.3%
With ammonia at 65℃;91%
With monomethanolamine In water at 0 - 60℃; for 48h;76%
(Z)-6-amino-9-(prop-1-en-1-yl)-9H-purine

(Z)-6-amino-9-(prop-1-en-1-yl)-9H-purine

(R)-9-(2-hydroxypropyl)adenine
14047-28-0

(R)-9-(2-hydroxypropyl)adenine

Conditions
ConditionsYield
With D-tartaric acid; 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; Concentration; Reagent/catalyst; Temperature;95.4%
9-propenyladenine
4121-40-8

9-propenyladenine

(R)-9-(2-hydroxypropyl)adenine
14047-28-0

(R)-9-(2-hydroxypropyl)adenine

Conditions
ConditionsYield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine) In dichloromethane at 15℃; for 5h; Temperature; Concentration;94.7%
(R)-5-amino-1-(2-hydroxypropyl)-1H-imidazole-4-carbonitrile
852954-49-5

(R)-5-amino-1-(2-hydroxypropyl)-1H-imidazole-4-carbonitrile

formamidine acetic acid
3473-63-0

formamidine acetic acid

(R)-9-(2-hydroxypropyl)adenine
14047-28-0

(R)-9-(2-hydroxypropyl)adenine

Conditions
ConditionsYield
With barium hydroxide monohydrate In N,N-dimethyl-formamide for 16h; Solvent; Concentration; Heating;93%
Conditions
ConditionsYield
With sodium hydroxide In N,N-dimethyl-formamide at 145℃; Temperature; Large scale;89.5%
With sodium hydroxide In N,N-dimethyl-formamide at 90 - 140℃; for 12h; Inert atmosphere;87%
With sodium hydroxide In N,N-dimethyl-formamide at 130 - 140℃; for 12h; Inert atmosphere;87%
(R)-9-<2-(2-tetrahydropyranyloxy)propyl>adenine
160616-02-4

(R)-9-<2-(2-tetrahydropyranyloxy)propyl>adenine

(R)-9-(2-hydroxypropyl)adenine
14047-28-0

(R)-9-(2-hydroxypropyl)adenine

Conditions
ConditionsYield
With sulfuric acid Ambient temperature;85%
7H-purin-6-ylamine
73-24-5

7H-purin-6-ylamine

(R)-1,2-propylene carbonate
16606-55-6

(R)-1,2-propylene carbonate

A

(R)-3-(2′-hydroxyprop-1-yl)adenine

(R)-3-(2′-hydroxyprop-1-yl)adenine

B

(R)-9-(2-hydroxypropyl)adenine
14047-28-0

(R)-9-(2-hydroxypropyl)adenine

Conditions
ConditionsYield
With sodium hydroxide In N,N-dimethyl-formamide for 8h; Reflux;A 8%
B 80%
Conditions
ConditionsYield
With sodium carbonate In N,N-dimethyl-formamide at 95℃; for 6h; Reagent/catalyst; Temperature;69%
1-(6-amino-9H-purin-9-yl)propan-2-one
105970-02-3

1-(6-amino-9H-purin-9-yl)propan-2-one

(R)-9-(2-hydroxypropyl)adenine
14047-28-0

(R)-9-(2-hydroxypropyl)adenine

Conditions
ConditionsYield
With dichloro(benzene)ruthenium(II) dimer; sodium formate; (R)-α,α-diphenylprolinol In acetonitrile at 20 - 30℃; for 48h; enantioselective reaction;64%
(R)-1-(5-Amino-6-chloro-pyrimidin-4-ylamino)-propan-2-ol
17435-30-2

(R)-1-(5-Amino-6-chloro-pyrimidin-4-ylamino)-propan-2-ol

(R)-9-(2-hydroxypropyl)adenine
14047-28-0

(R)-9-(2-hydroxypropyl)adenine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 86 percent / conc. HCl / Ambient temperature
2: 91 percent / NH3 / 65 °C
View Scheme
Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: pyridine; dmap / N,N-dimethyl-formamide / 10 h / 5 - 85 °C
2.1: 4 h / 130 °C
2.2: 2 h / 20 °C / pH 9 / Cooling
3.1: sodium hydroxide / water / 2 h / 93 °C
View Scheme
Conditions
ConditionsYield
Stage #1: adenine With sodium hydroxide In N,N-dimethyl-formamide at 20℃; for 0.333333h;
Stage #2: (R)-1,2-propylene carbonate at 120 - 130℃; for 16h;
A 97.9 %Chromat.
B 92.9 %Chromat.
7H-purin-6-ylamine
73-24-5

7H-purin-6-ylamine

(R)-propylene oxide
15448-47-2

(R)-propylene oxide

(R)-9-(2-hydroxypropyl)adenine
14047-28-0

(R)-9-(2-hydroxypropyl)adenine

Conditions
ConditionsYield
Stage #1: 7H-purin-6-ylamine With sodium hydroxide In water at 100 - 110℃; for 5h;
Stage #2: (R)-propylene oxide With ammonium chloride In water at 25℃; Reagent/catalyst; Solvent; Temperature;
5.5 g
6-chloropurine
87-42-3

6-chloropurine

(R)-9-(2-hydroxypropyl)adenine
14047-28-0

(R)-9-(2-hydroxypropyl)adenine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / Cooling with ice
1.2: 1 h / Cooling with ice
2.1: ruthenium; D-Prolin; sodium formate / acetonitrile / 24 h / 20 °C
3.1: monomethanolamine / water / 48 h / 0 - 60 °C
View Scheme
9-propenyladenine
4121-40-8

9-propenyladenine

A

(S)-1-(6-amino-9H-purin-9-yl) propan-2-ol
14047-27-9

(S)-1-(6-amino-9H-purin-9-yl) propan-2-ol

B

(R)-9-(2-hydroxypropyl)adenine
14047-28-0

(R)-9-(2-hydroxypropyl)adenine

Conditions
ConditionsYield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl In dichloromethane at 25℃; for 5h; Temperature; Concentration; Overall yield = 43.8 %; Overall yield = 4.2 g;
N6-acetyladenine
6034-68-0

N6-acetyladenine

(R)-9-(2-hydroxypropyl)adenine
14047-28-0

(R)-9-(2-hydroxypropyl)adenine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: formic acid ethyl ester / 7 h / Reflux
2: sodium hydroxide / water / 2 h / 70 °C
3: lithium ethoxide / tetrahydrofuran; ethanol / 0.5 h / 20 °C
4: (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane / 5 h / 15 °C
View Scheme
N6-acetyladenine
6034-68-0

N6-acetyladenine

A

(S)-1-(6-amino-9H-purin-9-yl) propan-2-ol
14047-27-9

(S)-1-(6-amino-9H-purin-9-yl) propan-2-ol

B

(R)-9-(2-hydroxypropyl)adenine
14047-28-0

(R)-9-(2-hydroxypropyl)adenine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: formic acid ethyl ester / 7 h / Reflux
2: sodium hydroxide / water / 2 h / 70 °C
3: lithium ethoxide / tetrahydrofuran; ethanol / 0.5 h / 20 °C
4: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl / dichloromethane / 5 h / 25 °C
View Scheme
C8H7N5O2

C8H7N5O2

(R)-9-(2-hydroxypropyl)adenine
14047-28-0

(R)-9-(2-hydroxypropyl)adenine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydroxide / water / 2 h / 70 °C
2: lithium ethoxide / tetrahydrofuran; ethanol / 0.5 h / 20 °C
3: (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane / 5 h / 15 °C
View Scheme
C8H7N5O2

C8H7N5O2

A

(S)-1-(6-amino-9H-purin-9-yl) propan-2-ol
14047-27-9

(S)-1-(6-amino-9H-purin-9-yl) propan-2-ol

B

(R)-9-(2-hydroxypropyl)adenine
14047-28-0

(R)-9-(2-hydroxypropyl)adenine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydroxide / water / 2 h / 70 °C
2: lithium ethoxide / tetrahydrofuran; ethanol / 0.5 h / 20 °C
3: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl / dichloromethane / 5 h / 25 °C
View Scheme
9-formyladenine

9-formyladenine

(R)-9-(2-hydroxypropyl)adenine
14047-28-0

(R)-9-(2-hydroxypropyl)adenine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: lithium ethoxide / tetrahydrofuran; ethanol / 0.5 h / 20 °C
2: (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane / 5 h / 15 °C
View Scheme
C8H11ClN4O2

C8H11ClN4O2

(R)-9-(2-hydroxypropyl)adenine
14047-28-0

(R)-9-(2-hydroxypropyl)adenine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride; trimethyl orthoformate / N,N-dimethyl-formamide; water / 20 - 30 °C
2: ammonium hydroxide / 1,4-dioxane / 100 - 110 °C / Sealed tube; Large scale
View Scheme
7H-purin-6-ylamine
73-24-5

7H-purin-6-ylamine

(R)-1,2-propylene carbonate
16606-55-6

(R)-1,2-propylene carbonate

(R)-9-(2-hydroxypropyl)adenine
14047-28-0

(R)-9-(2-hydroxypropyl)adenine

Conditions
ConditionsYield
With sodium hydroxide In N,N-dimethyl-formamide at 125 - 138℃;
5-amino-1-(2-hydroxypropyl)-1H-imidazole-4-carbonitrile

5-amino-1-(2-hydroxypropyl)-1H-imidazole-4-carbonitrile

(R)-9-(2-hydroxypropyl)adenine
14047-28-0

(R)-9-(2-hydroxypropyl)adenine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: barium hydroxide monohydrate / acetonitrile; water / 2 h / 25 °C
2: barium hydroxide monohydrate / N,N-dimethyl-formamide / 16 h / Heating
View Scheme
bis(2-propyl)-p-toluenesulfonyloxymethylphosphonate
35717-98-7

bis(2-propyl)-p-toluenesulfonyloxymethylphosphonate

(R)-9-(2-hydroxypropyl)adenine
14047-28-0

(R)-9-(2-hydroxypropyl)adenine

bis(2-propyl) (R)-9-(2-phosphonomethoxypropyl)adenine
160616-04-6

bis(2-propyl) (R)-9-(2-phosphonomethoxypropyl)adenine

Conditions
ConditionsYield
With magnesium 2-methylpropan-2-olate In water; N,N-dimethyl-formamide at -15 - 20℃; for 44h; Inert atmosphere;91%
With magnesium 2-methylpropan-2-olate In water; N,N-dimethyl-formamide at -15 - 20℃; for 44h; Inert atmosphere;
diethyl (p-toluenesulfonyloxymethane)phosphonate
31618-90-3

diethyl (p-toluenesulfonyloxymethane)phosphonate

(R)-9-(2-hydroxypropyl)adenine
14047-28-0

(R)-9-(2-hydroxypropyl)adenine

(S)-9-(2-phosphonylmethoxypropyl)adenine
147127-19-3

(S)-9-(2-phosphonylmethoxypropyl)adenine

Conditions
ConditionsYield
Stage #1: (R)-9-(2-hydroxypropyl)adenine With bis(isopropoxy) magnesium In N,N-dimethyl-formamide at 65℃; for 1h; Inert atmosphere;
Stage #2: diethyl (p-toluenesulfonyloxymethane)phosphonate In N,N-dimethyl-formamide at 45 - 55℃; for 10h;
Stage #3: With hydrogenchloride In water at 90℃; for 10h;
88%
diethyl (p-toluenesulfonyloxymethane)phosphonate
31618-90-3

diethyl (p-toluenesulfonyloxymethane)phosphonate

(R)-9-(2-hydroxypropyl)adenine
14047-28-0

(R)-9-(2-hydroxypropyl)adenine

(R)-diethyl (((1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonate
180587-75-1

(R)-diethyl (((1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonate

Conditions
ConditionsYield
With magnesium 2-methylpropan-2-olate In N,N-dimethyl-formamide at 80℃; for 5h; Solvent;85%
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃;44%
Stage #1: (R)-9-(2-hydroxypropyl)adenine With sodium t-butanolate In N,N-dimethyl-formamide at 20℃; for 1h;
Stage #2: diethyl (p-toluenesulfonyloxymethane)phosphonate In N,N-dimethyl-formamide for 64h;
29%
{[(4-methylbenzenesulfonyl)oxy]methyl}phosphonic acid
161760-09-4

{[(4-methylbenzenesulfonyl)oxy]methyl}phosphonic acid

(R)-9-(2-hydroxypropyl)adenine
14047-28-0

(R)-9-(2-hydroxypropyl)adenine

A

C9H14N5O4P

C9H14N5O4P

B

tenofovir
147127-20-6

tenofovir

Conditions
ConditionsYield
In 1-methyl-pyrrolidin-2-one at 0 - 20℃; Solvent; Reagent/catalyst; Temperature; Inert atmosphere; Molecular sieve;A 12%
B 82%
(R)-9-(2-hydroxypropyl)adenine
14047-28-0

(R)-9-(2-hydroxypropyl)adenine

tenofovir
147127-20-6

tenofovir

C17H23N10O4P

C17H23N10O4P

Conditions
ConditionsYield
With dmap; triethylamine; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 90℃; Inert atmosphere;77.8%
With dmap; triethylamine; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 90℃; Inert atmosphere;55%
(di-tert-butoxyphosphoryl)methyl methanesulfonate

(di-tert-butoxyphosphoryl)methyl methanesulfonate

(R)-9-(2-hydroxypropyl)adenine
14047-28-0

(R)-9-(2-hydroxypropyl)adenine

tenofovir
147127-20-6

tenofovir

Conditions
ConditionsYield
Stage #1: (R)-9-(2-hydroxypropyl)adenine With magnesium 2-methylpropan-2-olate In N,N-dimethyl acetamide at 90℃; for 0.5h; Schlenk technique; Inert atmosphere;
Stage #2: (di-tert-butoxyphosphoryl)methyl methanesulfonate In N,N-dimethyl acetamide at 90℃; for 23h; Schlenk technique; Inert atmosphere;
Stage #3: With sulfuric acid at 60℃; Reagent/catalyst; Schlenk technique; Inert atmosphere;
72%
{[(4-methylbenzenesulfonyl)oxy]methyl}phosphonic acid
161760-09-4

{[(4-methylbenzenesulfonyl)oxy]methyl}phosphonic acid

(R)-9-(2-hydroxypropyl)adenine
14047-28-0

(R)-9-(2-hydroxypropyl)adenine

A

C10H17N5O7P2

C10H17N5O7P2

B

tenofovir
147127-20-6

tenofovir

Conditions
ConditionsYield
With magnesium chloride In 1-methyl-pyrrolidin-2-one at -20 - 20℃; Inert atmosphere;A 6%
B 69%
(di-tert-butoxyphosphoryl)methyl 4-methylbenzenesulfonate

(di-tert-butoxyphosphoryl)methyl 4-methylbenzenesulfonate

(R)-9-(2-hydroxypropyl)adenine
14047-28-0

(R)-9-(2-hydroxypropyl)adenine

tenofovir
147127-20-6

tenofovir

Conditions
ConditionsYield
Stage #1: (R)-9-(2-hydroxypropyl)adenine With magnesium 2-methylpropan-2-olate In N,N-dimethyl-formamide at 80℃; Schlenk technique; Inert atmosphere;
Stage #2: (di-tert-butoxyphosphoryl)methyl 4-methylbenzenesulfonate In N,N-dimethyl-formamide at 80℃; for 23h; Schlenk technique; Inert atmosphere;
Stage #3: With sulfuric acid at 60℃; Schlenk technique; Inert atmosphere;
68%
{[(4-methylbenzenesulfonyl)oxy]methyl}phosphonic acid
161760-09-4

{[(4-methylbenzenesulfonyl)oxy]methyl}phosphonic acid

(R)-9-(2-hydroxypropyl)adenine
14047-28-0

(R)-9-(2-hydroxypropyl)adenine

A

C10H17N5O7P2

C10H17N5O7P2

B

C9H14N5O4P

C9H14N5O4P

C

tenofovir
147127-20-6

tenofovir

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;A 8%
B 11%
C 64%
diethyl (p-toluenesulfonyloxymethane)phosphonate
31618-90-3

diethyl (p-toluenesulfonyloxymethane)phosphonate

(R)-9-(2-hydroxypropyl)adenine
14047-28-0

(R)-9-(2-hydroxypropyl)adenine

tenofovir
147127-20-6

tenofovir

Conditions
ConditionsYield
With bis(isopropoxy) magnesium In N,N-dimethyl-formamide at 45 - 65℃; for 11h; Autoclave; Inert atmosphere; Large scale;59.2%
Stage #1: diethyl (p-toluenesulfonyloxymethane)phosphonate; (R)-9-(2-hydroxypropyl)adenine With magnesium 2-methylpropan-2-olate In 1-methyl-pyrrolidin-2-one; toluene at 25 - 75℃; for 6h;
Stage #2: With water; acetic acid In 1-methyl-pyrrolidin-2-one; water; acetic acid; toluene for 1h;
Stage #3: With hydrogen bromide In 1-methyl-pyrrolidin-2-one; water; toluene at 90 - 95℃;
Stage #1: (R)-9-(2-hydroxypropyl)adenine With magnesium 2-methylpropan-2-olate In N,N-dimethyl-formamide at 20 - 35℃; for 0.5h;
Stage #2: diethyl (p-toluenesulfonyloxymethane)phosphonate In N,N-dimethyl-formamide at 75 - 80℃; for 2h;
Stage #3: With hydrogenchloride In N,N-dimethyl-formamide at 0 - 95℃; for 9h; Temperature; Reagent/catalyst;
82 g
With trimethylsilyl bromide; water; sodium hydroxide In dichloromethane at 0 - 5℃; for 3h; pH=2.5 - 3;
Stage #1: diethyl (p-toluenesulfonyloxymethane)phosphonate; (R)-9-(2-hydroxypropyl)adenine With alumina-supported potassium hydroxide In N,N-dimethyl-formamide at 40 - 130℃; for 18h;
Stage #2: With water at 100 - 105℃; for 18h; Reagent/catalyst; Temperature; Solvent;
2-(2-(2-methoxyethoxy)ethoxy)ethyl p-toluenesulfonate
62921-74-8

2-(2-(2-methoxyethoxy)ethoxy)ethyl p-toluenesulfonate

(R)-9-(2-hydroxypropyl)adenine
14047-28-0

(R)-9-(2-hydroxypropyl)adenine

C15H25N5O4

C15H25N5O4

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 7h;49.4%
benzoyl chloride
98-88-4

benzoyl chloride

(R)-9-(2-hydroxypropyl)adenine
14047-28-0

(R)-9-(2-hydroxypropyl)adenine

(R)-9-(2-hydroxypropyl)-N6-benzoyladenine
160616-03-5

(R)-9-(2-hydroxypropyl)-N6-benzoyladenine

Conditions
ConditionsYield
With chloro-trimethyl-silane 1) pyridine, room temperature, 1 h; 2) pyridine, room temperature, 2 h; Yield given. Multistep reaction;
(R)-9-(2-hydroxypropyl)adenine
14047-28-0

(R)-9-(2-hydroxypropyl)adenine

(R)-9-[2-(phosphanylmethoxy)propyl]adenine
919512-64-4

(R)-9-[2-(phosphanylmethoxy)propyl]adenine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium tert-butoxide / dimethylformamide / 1 h / 20 °C
1.2: 740 mg / dimethylformamide / 64 h / 20 °C
2.1: 65 percent / TMSCl; LiAlH4 / tetrahydrofuran / 2 h / 20 °C
View Scheme
(R)-9-(2-hydroxypropyl)adenine
14047-28-0

(R)-9-(2-hydroxypropyl)adenine

({[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methyl)phosphinic acid
919512-65-5

({[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methyl)phosphinic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium tert-butoxide / dimethylformamide / 1 h / 20 °C
1.2: 740 mg / dimethylformamide / 64 h / 20 °C
2.1: 65 percent / TMSCl; LiAlH4 / tetrahydrofuran / 2 h / 20 °C
3.1: 100 percent / aq. H2O2 / tetrahydrofuran / 1 h / 20 °C
View Scheme
(R)-9-(2-hydroxypropyl)adenine
14047-28-0

(R)-9-(2-hydroxypropyl)adenine

C15H30N5O3PSi2

C15H30N5O3PSi2

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium tert-butoxide / dimethylformamide / 1 h / 20 °C
1.2: 740 mg / dimethylformamide / 64 h / 20 °C
2.1: 65 percent / TMSCl; LiAlH4 / tetrahydrofuran / 2 h / 20 °C
3.1: 100 percent / aq. H2O2 / tetrahydrofuran / 1 h / 20 °C
4.1: tetrahydrofuran / 1 h / 20 °C
View Scheme
(R)-9-(2-hydroxypropyl)adenine
14047-28-0

(R)-9-(2-hydroxypropyl)adenine

tenofovir
147127-20-6

tenofovir

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: LiOt-Bu / dimethylformamide; tetrahydrofuran / 1 h / 30 - 35 °C
2: 1.) bromotrimethylsilane, 2.) NaOH / 1.) acetonitrile, reflux, 2.) H2O, pH 3
View Scheme
Multi-step reaction with 2 steps
1: 44 percent / NaH / dimethylformamide / 0 - 20 °C
2: 1.) TMSBr, 2.) H2O / 1.) MeCN, RT, 2.) acetone, 4 deg C
View Scheme
Multi-step reaction with 4 steps
1: 1.) chlorotrimethylsilane / 1) pyridine, room temperature, 1 h; 2) pyridine, room temperature, 2 h
2: sodium hydride / dimethylformamide / 48 h / Ambient temperature
3: sodium methoxide / dimethylformamide / Ambient temperature
4: 47 percent / bromotrimethylsilane / acetonitrile / Ambient temperature
View Scheme
(R)-9-(2-hydroxypropyl)adenine
14047-28-0

(R)-9-(2-hydroxypropyl)adenine

bis(2-propyl) (R)-9-(2-phosphonomethoxypropyl)adenine
160616-04-6

bis(2-propyl) (R)-9-(2-phosphonomethoxypropyl)adenine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) chlorotrimethylsilane / 1) pyridine, room temperature, 1 h; 2) pyridine, room temperature, 2 h
2: sodium hydride / dimethylformamide / 48 h / Ambient temperature
3: sodium methoxide / dimethylformamide / Ambient temperature
View Scheme
(R)-9-(2-hydroxypropyl)adenine
14047-28-0

(R)-9-(2-hydroxypropyl)adenine

[(R)-2-(6-Benzoylamino-purin-9-yl)-1-methyl-ethoxymethyl]-phosphonic acid diisopropyl ester
627510-49-0

[(R)-2-(6-Benzoylamino-purin-9-yl)-1-methyl-ethoxymethyl]-phosphonic acid diisopropyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) chlorotrimethylsilane / 1) pyridine, room temperature, 1 h; 2) pyridine, room temperature, 2 h
2: sodium hydride / dimethylformamide / 48 h / Ambient temperature
View Scheme
(R)-9-(2-hydroxypropyl)adenine
14047-28-0

(R)-9-(2-hydroxypropyl)adenine

A

C15H24N5O8P
1244022-55-6

C15H24N5O8P

B

C20H32N5O11P
1244022-53-4

C20H32N5O11P

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: magnesium 2-methylpropan-2-olate / 1-methyl-pyrrolidin-2-one / 70 - 74 °C
2.1: chloro-trimethyl-silane; sodium bromide / 1-methyl-pyrrolidin-2-one / 0 - 75 °C
3.1: triethylamine / 1-methyl-pyrrolidin-2-one / 45 °C
3.2: 5.5 h / 45 - 50 °C
View Scheme

(R)-(+)-9-(2-Hydroxypropyl)adenine Chemical Properties

Product Name: (R)-(+)-9-(2-Hydroxypropyl)adenine (CAS NO.14047-28-0)


Molecular Formula: C8H11N5O
Molecular Weight: 193.21g/mol
Mol File: 14047-28-0.mol
Melting Point: 193 °C
Boiling point: 457.7 °C at 760 mmHg
Flash Point: 230.6 °C
Density: 1.57 g/cm3
Surface Tension: 68.5 dyne/cm
Enthalpy of Vaporization: 75.64 kJ/mol
Vapour Pressure: 3.6E-09 mmHg at 25°C
Product Categories: Chiral Reagents; Bases & Related Reagents; Nucleotides

(R)-(+)-9-(2-Hydroxypropyl)adenine Specification

 (R)-(+)-9-(2-Hydroxypropyl)adenine , its CAS NO. is 14047-28-0, the synonyms are R-9-(2-hydroxypropyl) adenine, 9-HPA ; (R)-(+)-9-(2-Hydroxypropyl)adenine ; 6-Amino-alpha-methyl-9H-purine-9-ethanol ; D-(-)-9-(2-Hydroxypropyl)adenine .

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