(R)-9-(2-hydroxypropyl)adenine
Conditions | Yield |
---|---|
With sodium hydroxide In water at 93℃; for 2h; Temperature; | 97.7% |
(R)-1-(6-chloro-9H-purin-9-yl) propan-2-ol
(R)-9-(2-hydroxypropyl)adenine
Conditions | Yield |
---|---|
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% |
(R)-9-(2-hydroxypropyl)adenine
Conditions | Yield |
---|---|
With D-tartaric acid; 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; Concentration; Reagent/catalyst; Temperature; | 95.4% |
9-propenyladenine
(R)-9-(2-hydroxypropyl)adenine
Conditions | Yield |
---|---|
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
formamidine acetic acid
(R)-9-(2-hydroxypropyl)adenine
Conditions | Yield |
---|---|
With barium hydroxide monohydrate In N,N-dimethyl-formamide for 16h; Solvent; Concentration; Heating; | 93% |
Conditions | Yield |
---|---|
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
(R)-9-(2-hydroxypropyl)adenine
Conditions | Yield |
---|---|
With sulfuric acid Ambient temperature; | 85% |
7H-purin-6-ylamine
(R)-1,2-propylene carbonate
B
(R)-9-(2-hydroxypropyl)adenine
Conditions | Yield |
---|---|
With sodium hydroxide In N,N-dimethyl-formamide for 8h; Reflux; | A 8% B 80% |
Conditions | Yield |
---|---|
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
(R)-9-(2-hydroxypropyl)adenine
Conditions | Yield |
---|---|
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
(R)-9-(2-hydroxypropyl)adenine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 86 percent / conc. HCl / Ambient temperature 2: 91 percent / NH3 / 65 °C View Scheme |
(R)-9-(2-hydroxypropyl)adenine
Conditions | Yield |
---|---|
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 | Yield |
---|---|
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. |
Conditions | Yield |
---|---|
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
(R)-9-(2-hydroxypropyl)adenine
Conditions | Yield |
---|---|
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
A
(S)-1-(6-amino-9H-purin-9-yl) propan-2-ol
B
(R)-9-(2-hydroxypropyl)adenine
Conditions | Yield |
---|---|
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
(R)-9-(2-hydroxypropyl)adenine
Conditions | Yield |
---|---|
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
A
(S)-1-(6-amino-9H-purin-9-yl) propan-2-ol
B
(R)-9-(2-hydroxypropyl)adenine
Conditions | Yield |
---|---|
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 |
(R)-9-(2-hydroxypropyl)adenine
Conditions | Yield |
---|---|
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 |
A
(S)-1-(6-amino-9H-purin-9-yl) propan-2-ol
B
(R)-9-(2-hydroxypropyl)adenine
Conditions | Yield |
---|---|
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 |
(R)-9-(2-hydroxypropyl)adenine
Conditions | Yield |
---|---|
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 |
(R)-9-(2-hydroxypropyl)adenine
Conditions | Yield |
---|---|
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
(R)-1,2-propylene carbonate
(R)-9-(2-hydroxypropyl)adenine
Conditions | Yield |
---|---|
With sodium hydroxide In N,N-dimethyl-formamide at 125 - 138℃; |
(R)-9-(2-hydroxypropyl)adenine
Conditions | Yield |
---|---|
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
(R)-9-(2-hydroxypropyl)adenine
bis(2-propyl) (R)-9-(2-phosphonomethoxypropyl)adenine
Conditions | Yield |
---|---|
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
(R)-9-(2-hydroxypropyl)adenine
(S)-9-(2-phosphonylmethoxypropyl)adenine
Conditions | Yield |
---|---|
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
(R)-9-(2-hydroxypropyl)adenine
(R)-diethyl (((1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonate
Conditions | Yield |
---|---|
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
(R)-9-(2-hydroxypropyl)adenine
B
tenofovir
Conditions | Yield |
---|---|
In 1-methyl-pyrrolidin-2-one at 0 - 20℃; Solvent; Reagent/catalyst; Temperature; Inert atmosphere; Molecular sieve; | A 12% B 82% |
Conditions | Yield |
---|---|
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% |
(R)-9-(2-hydroxypropyl)adenine
tenofovir
Conditions | Yield |
---|---|
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
(R)-9-(2-hydroxypropyl)adenine
B
tenofovir
Conditions | Yield |
---|---|
With magnesium chloride In 1-methyl-pyrrolidin-2-one at -20 - 20℃; Inert atmosphere; | A 6% B 69% |
(R)-9-(2-hydroxypropyl)adenine
tenofovir
Conditions | Yield |
---|---|
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
(R)-9-(2-hydroxypropyl)adenine
C
tenofovir
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 20℃; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; | A 8% B 11% C 64% |
diethyl (p-toluenesulfonyloxymethane)phosphonate
(R)-9-(2-hydroxypropyl)adenine
tenofovir
Conditions | Yield |
---|---|
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
(R)-9-(2-hydroxypropyl)adenine
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 7h; | 49.4% |
benzoyl chloride
(R)-9-(2-hydroxypropyl)adenine
(R)-9-(2-hydroxypropyl)-N6-benzoyladenine
Conditions | Yield |
---|---|
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
(R)-9-[2-(phosphanylmethoxy)propyl]adenine
Conditions | Yield |
---|---|
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
({[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methyl)phosphinic acid
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
tenofovir
Conditions | Yield |
---|---|
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
bis(2-propyl) (R)-9-(2-phosphonomethoxypropyl)adenine
Conditions | Yield |
---|---|
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
[(R)-2-(6-Benzoylamino-purin-9-yl)-1-methyl-ethoxymethyl]-phosphonic acid diisopropyl ester
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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 |
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 , 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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