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inquiry2-acetoxyethyl acetoxymethyl ether
2,9-diacetylguanine
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
Conditions | Yield |
---|---|
at 105℃; for 80h; | 95.1% |
With toluene-4-sulfonic acid In toluene at 110℃; Temperature; Large scale; | 94.3% |
2-acetoxyethyl acetoxymethyl ether
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
Conditions | Yield |
---|---|
In methanol; dichloromethane | 94% |
2-acetoxyethyl acetoxymethyl ether
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
Conditions | Yield |
---|---|
In methanol; toluene | 91% |
2-acetoxyethyl acetoxymethyl ether
acetic anhydride
G
A
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
B
7-<(2-acetoxyethoxy)methyl>-N2-acetylguanine
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid at 100℃; for 20h; | A 86% B 0.5% |
With sulfuric acid at 100℃; for 24h; Product distribution; other acid caclysts, temperature time, solvents; transpurination reaction of guanosine under various conditions; | A 43% B 35% |
With phosphoric acid at 100℃; for 24h; Title compound not separated from byproducts; | A 47 % Chromat. B 38 % Chromat. |
acycloguanosine
acetic anhydride
A
9-[(acetoxyethoxy)methyl]guanine
B
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
Conditions | Yield |
---|---|
With dmap In N,N-dimethyl-formamide Acetylation; | A 84% B 4% |
9-<(2-acetoxyethoxy)methyl>-2-acetylamino-6-(p-fluorobenzenesulfonyloxy)-9H-purine
A
9-[(acetoxyethoxy)methyl]guanine
B
9-<(2-acetoxyethoxy)methyl>-2-acetylamino-9H-purine
C
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
Conditions | Yield |
---|---|
With palladium diacetate; 1,3-bis-(diphenylphosphino)propane; triethylammonium formate In 1,4-dioxane at 90℃; for 0.5h; | A 0.3% B 80.4% C 19.3% |
9-[(acetoxyethoxy)methyl]guanine
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
Conditions | Yield |
---|---|
With dmap In hexane; acetic anhydride; toluene | 79% |
acycloguanosine
acetic anhydride
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
Conditions | Yield |
---|---|
With pyridine for 1h; Heating; | 75% |
2-hydroxyethyl acetate
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
Conditions | Yield |
---|---|
With bis(tertbutylcarbonyloxy)iodobenzene; palladium diacetate In toluene at 90℃; for 24h; | 70% |
N-(6-oxo-6,9-dihydro-1H-purin-2-yl)acetamide
2-acetoxyethyl acetoxymethyl ether
1,1,1,3,3,3-hexamethyl-disilazane
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
Conditions | Yield |
---|---|
Stage #1: N-(6-oxo-6,9-dihydro-1H-purin-2-yl)acetamide; 1,1,1,3,3,3-hexamethyl-disilazane With ammonium sulfate for 2h; Heating; Stage #2: 2-acetoxyethyl acetoxymethyl ether; iodine-doped natural phosphate In acetonitrile Heating; Further stages.; | 34% |
Stage #1: N-(6-oxo-6,9-dihydro-1H-purin-2-yl)acetamide; 1,1,1,3,3,3-hexamethyl-disilazane With ammonium sulfate Heating; Stage #2: 2-acetoxyethyl acetoxymethyl ether; natural phosphate; zinc dibromide In acetonitrile for 2h; Heating; | 10% |
1,3-DIOXOLANE
acetic anhydride
2,9-diacetylguanine
A
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
B
7-<(2-acetoxyethoxy)methyl>-N2-acetylguanine
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid; acetic acid In toluene at 120℃; for 2.5h; | A 29% B 29% |
2-acetoxyethyl acetoxymethyl ether
toluene-4-sulfonic acid
7-<(2-acetoxyethoxy)methyl>-N2-acetylguanine
A
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
Conditions | Yield |
---|---|
In chlorobenzene at 130℃; Substitution; | A 28% B 8% |
Acetic acid 2-(2-oxo-propoxy)-ethyl ester
2,9-diacetylguanine
A
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
B
7-<(2-acetoxyethoxy)methyl>-N2-acetylguanine
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid 1.) 120-125 deg C, 2.) 150 deg C, 45 min; | A 27% B 22% |
2-acetoxyethyl acetoxymethyl ether
G
A
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
B
7-<(2-acetoxyethoxy)methyl>-N2-acetylguanine
Conditions | Yield |
---|---|
With acetic anhydride; toluene-4-sulfonic acid at 100℃; for 20h; | A 22% B 20% |
1,3-DIOXOLANE
2,9-diacetylguanine
A
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
B
7-<(2-acetoxyethoxy)methyl>-N2-acetylguanine
Conditions | Yield |
---|---|
With acetic anhydride; toluene-4-sulfonic acid In acetic acid for 1h; Heating; | A 18% B 2.3% |
2-amino-1,9-dihydro-6H-purin-6-one
2-acetoxyethyl acetoxymethyl ether
acetic anhydride
A
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
B
7-<(2-acetoxyethoxy)methyl>-N2-acetylguanine
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid 1.) acetic acid, 140 deg C, 18 h, 2.) DMSO, 100 deg C, 16 h; Yield given. Multistep reaction. Yields of byproduct given; |
2-methoxy-ethanol
acetic anhydride
2,9-diacetylguanine
A
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
B
7-<(2-acetoxyethoxy)methyl>-N2-acetylguanine
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid 1.) AcOH, 2.) toluene, reflux, 16 h; Yield given. Multistep reaction. Yields of byproduct given; |
9-<(2-acetoxyethoxy)methyl>-2-acetylamino-6-(p-toluenesulfonyloxy)-9H-purine
A
9-[(acetoxyethoxy)methyl]guanine
B
9-<(2-acetoxyethoxy)methyl>-2-acetylamino-9H-purine
C
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
Conditions | Yield |
---|---|
With hydrogen; Lindlar's catalyst In ethanol at 70℃; for 24h; Further byproducts given; | A 6.6 % Chromat. B 87.3 % Chromat. C 1.0 % Chromat. D 4.7 % Chromat. |
9-<(2-acetoxyethoxy)methyl>-2-acetylamino-6-(p-fluorobenzenesulfonyloxy)-9H-purine
A
9-<(2-acetoxyethoxy)methyl>-2-amino-9H-purine
B
9-[(acetoxyethoxy)methyl]guanine
C
2-acetylamino-9-<(2-hydroxyethoxy)methyl>-1,9-dihydro-6H-purin-6-one
D
9-<(2-acetoxyethoxy)methyl>-2-acetylamino-9H-purine
E
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In ethanol at 70℃; for 1h; Product distribution; other reagents; | A 6.0 % Chromat. B 1.2 % Chromat. C 0.8 % Chromat. D 74.7 % Chromat. E 12.3 % Chromat. F 4.7 % Chromat. |
9-<(2-acetoxyethoxy)methyl>-2-acetylamino-6-(p-fluorobenzenesulfonyloxy)-9H-purine
A
2-acetylamino-9-<(2-hydroxyethoxy)methyl>-1,9-dihydro-6H-purin-6-one
B
9-<(2-acetoxyethoxy)methyl>-2-acetylamino-9H-purine
C
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
Conditions | Yield |
---|---|
With palladium diacetate; triethylammonium formate; triphenylphosphine In 1,4-dioxane at 90℃; for 1h; Further byproducts given; | A 3.0 % Chromat. B 57.6 % Chromat. C 18.2 % Chromat. D 20.8 % Chromat. |
9-<(2-acetoxyethoxy)methyl>-2-acetylamino-6-(2,4,6-trimethylbenzenesulfonyloxy)-9H-purine
A
9-[(acetoxyethoxy)methyl]guanine
B
9-<(2-acetoxyethoxy)methyl>-2-acetylamino-9H-purine
C
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
Conditions | Yield |
---|---|
With hydrogen; Lindlar's catalyst In ethanol at 70℃; for 24h; Further byproducts given; | A 2.2 % Chromat. B 91.8 % Chromat. C 1.1 % Chromat. D 4.5 % Chromat. |
Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(2-acetylamino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester
2-acetoxyethyl acetoxymethyl ether
A
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
B
7-<(2-acetoxyethoxy)methyl>-N2-acetylguanine
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid at 100℃; for 48h; | A 42 % Chromat. B 30 % Chromat. |
7-<(2-acetoxyethoxy)methyl>-N2-acetylguanine
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
Conditions | Yield |
---|---|
at 90 - 100℃; under 30 Torr; for 22.5h; |
Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(2-acetylamino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester
2-acetoxyethyl acetoxymethyl ether
A
7-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-N2-acetylguanine
B
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
C
7-<(2-acetoxyethoxy)methyl>-N2-acetylguanine
Conditions | Yield |
---|---|
In chlorobenzene; acetonitrile at 120℃; for 2h; Mechanism; | |
With toluene-4-sulfonic acid In chlorobenzene; acetonitrile at 120℃; for 2h; |
7-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-N2-acetylguanine
2-acetoxyethyl acetoxymethyl ether
A
Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(2-acetylamino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester
B
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
C
7-<(2-acetoxyethoxy)methyl>-N2-acetylguanine
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In chlorobenzene; acetonitrile at 120℃; for 2h; |
A
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
B
7-<(2-acetoxyethoxy)methyl>-N2-acetylguanine
Conditions | Yield |
---|---|
at 210℃; for 0.0833333h; Decomposition; | |
In chlorobenzene at 70℃; for 2h; Decomposition; |
2-amino-1,9-dihydro-6H-purin-6-one
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: triflic acid / 32 h / 160 °C 1.2: 93 percent / 12 h / Heating 2.1: 85 percent / acetic acid / H2O / 2 h / 80 °C 3.1: 75 percent / pyridine / 1 h / Heating View Scheme |
9-(2-trimethylsilyloxyethoxymethyl)guanine
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 85 percent / acetic acid / H2O / 2 h / 80 °C 2: 75 percent / pyridine / 1 h / Heating View Scheme |
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
acycloguanosine
Conditions | Yield |
---|---|
With sodium hydroxide In water at 85 - 95℃; for 3h; | 97.5% |
With methylamine In water at 23℃; for 1h; | 93% |
With sodium hydroxide | 92% |
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
9-[(acetoxyethoxy)methyl]guanine
Conditions | Yield |
---|---|
With triethylamine In ethanol for 10h; Heating; | 97% |
With triethanolamine In methanol | 92% |
With methanol; sodium methylate for 16h; Ambient temperature; | 81% |
With Schwartz's reagent In tetrahydrofuran at 20℃; Inert atmosphere; chemoselective reaction; | 47% |
Multi-step reaction with 2 steps 1: 81 percent / DMAP, Et3N / CH2Cl2 / 1 h / Ambient temperature 2: 2.2 percent Chromat. / hydrogen / Pd/CaCO3 / ethanol / 24 h / 70 °C View Scheme |
2,4,6-triisopropylphenylsulfonyl chloride
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
9-<(2-acetoxyethoxy)methyl>-2-acetylamino-6-(2,4,6-triisopropylbenzenesulfonyloxy)-9H-purine
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane Ambient temperature; | 95% |
ammonium hydroxide
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
acycloguanosine
Conditions | Yield |
---|---|
In methanol | 90% |
2-mesitylenesulphonyl chloride
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
9-<(2-acetoxyethoxy)methyl>-2-acetylamino-6-(2,4,6-trimethylbenzenesulfonyloxy)-9H-purine
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane for 1h; Ambient temperature; | 81% |
potassium tetrachloroplatinate(II)
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
C24H30Cl2N10O10Pt
Conditions | Yield |
---|---|
In water molar ratio K2PtCl4:ligand = 1:2, suspension stirred at room temp. for 3 d; washed with water, methanol, ether; elem. anal.; | 80% |
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
diphenylcarbamic chloride
9-<(2-acetoxyethoxy)methyl>-2-N-acetyl-6-O-(diphenylcarbamoyl)guanine
Conditions | Yield |
---|---|
With pyridine; N-ethyl-N,N-diisopropylamine at 20℃; for 4h; | 77% |
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
p-toluenesulfonyl chloride
9-<(2-acetoxyethoxy)methyl>-2-acetylamino-6-(p-toluenesulfonyloxy)-9H-purine
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane for 10h; Ambient temperature; | 74% |
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
2-((2-acetamido-6-thioxo-1,6-dihydro-9H-purin-9-yl)methoxy)ethyl acetate
Conditions | Yield |
---|---|
With [p-CH3OC6H4P(S)S]2 In pyridine for 7h; Heating; | 74% |
With diphosphorus pentasulfide In pyridine | 65% |
4-Fluorobenzenesulfonyl chloride
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
9-<(2-acetoxyethoxy)methyl>-2-acetylamino-6-(p-fluorobenzenesulfonyloxy)-9H-purine
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane for 24h; Ambient temperature; | 70% |
potassium trichloro(ethene)platinate(II)
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
trans-{PtCl2(η(2)-C2H4)(9-(2-acetoxyethoxymethyl)-N(2)-acetylguanine)}
Conditions | Yield |
---|---|
In methanol stoich. amt. of C12H15N5O5, 2 h of stirring at 0°C, evapn. of solvent in vac.; dissolved in the min. amt. of dichloromethane, filtered, solvent slowly evapd. in vac.; elem. anal.; | 70% |
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
2-acetylamino-9-<(2-hydroxyethoxy)methyl>-1,9-dihydro-6H-purin-6-one
Conditions | Yield |
---|---|
With sodium methylate In methanol at 23℃; for 0.266667h; | 67% |
With methanol; sodium at 21℃; for 0.266667h; | 57% |
With ammonium hydroxide at 50℃; for 1h; | 55% |
cis-bis(dimethylsulfoxide)dichloroplatinum(II)
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
trans-(PtCl2(DMSO)(9-(2-acetoxyethoxymethyl)-N(2)-acetylguanine))
cis-(PtCl2(DMSO)(9-(2-acetoxyethoxymethyl)-N(2)-acetylguanine))
Conditions | Yield |
---|---|
In methanol stoich. amt., stirring for 1 day; redn. of vol., filtration, excess of diethyl ether, pptn.; elem. anal.; | A 65% B n/a |
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
benzyl bromide
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 16h; Alkylation; | A 50% B 13% |
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
9-<(2-acetoxyethoxy)methyl>-2-acetylamino-6-chloro-9H-purine
Conditions | Yield |
---|---|
With 2,4,6-trimethyl-pyridine; tetraethylammonium chloride; trichlorophosphate In acetonitrile for 0.166667h; Heating; | 37% |
With N,N-diethylaniline; trichlorophosphate In acetonitrile |
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
methyl iodide
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 16h; Methylation; | A 8% B 4% C 33% |
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
Conditions | Yield |
---|---|
With fluorine In chloroform for 1h; Ambient temperature; | 30% |
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