75128-73-3

Basic information

• Product Name: 9-[(2-Acetoxyethoxy)methyl]-N2-acetylguanine
• Synonyms: 2-Acetamido-9-{[2-(acetyloxy)ethoxy]methyl}hypoxathine;2-Acetyl-9-{[2-(acetyloxy)ethyl]methyl}guanine;n-(9-((2-(acetyloxy)ethoxy)methyl)-6,9-dihydro-6-oxo-1h-purin-2-yl)acetamide;N2-ACETYL-9-[(2'-ACETOXYETHOXY)METHYL]GUANINE;SALOR-INT L254681-1EA;2-[(2-acetamido-6-oxo-6,9-dihydro-1h-purin-9-yl)methoxy]ethyl acetate;2-[[(2-ACETYLAMINO)-6-OXO-1,6-DIHYDRO-9H-PURIN-9-YL]-METHOXY] ETHYL ACETATE;ACYCLOVIR IMPURITY G
• CAS NO: 75128-73-3
• Molecular Formula: C₁₂H₁₅N₅O₅
• Molecular Weight: 309.28
• EINECS: 278-077-7
• Product Categories: Active Pharmaceutical Ingredients;Heterocyclic Compounds;Heterocycles;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 75128-73-3.mol
• Article Data: 21

Chemical Properties

• Melting Point: 204°C
• Appearance: white to light yellow crystal powder
• Density: 1.53
• Refractive Index: 1.654
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 8.77±0.20(Predicted)
• CAS DataBase Reference: 9-[(2-Acetoxyethoxy)methyl]-N2-acetylguanine(CAS DataBase Reference)
• NIST Chemistry Reference: 9-[(2-Acetoxyethoxy)methyl]-N2-acetylguanine(75128-73-3)
• EPA Substance Registry System: 9-[(2-Acetoxyethoxy)methyl]-N2-acetylguanine(75128-73-3)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36-37/39
• Hazardous Substances Data: 75128-73-3(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

Uses

An impurity of Acyclovir

InChI:InChI=1/C12H15N5O5/c1-7(18)14-12-15-10-9(11(20)16-12)13-5-17(10)6-21-3-4-22-8(2)19/h5H,3-4,6H2,1-2H3,(H2,14,15,16,18,20)

Synthetic route

2-acetoxyethyl acetoxymethyl ether (59278-00-1) + 2,9-diacetylguanine (3056-33-5) → 2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one (75128-73-3)

Conditions	Yield
at 105℃; for 80h;	95.1%
With toluene-4-sulfonic acid In toluene at 110℃; Temperature; Large scale;	94.3%

diacetyl guanine + 2-acetoxyethyl acetoxymethyl ether (59278-00-1) → 2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one (75128-73-3)

Conditions	Yield
In methanol; dichloromethane	94%

diacetylguanine + diacetyl guanine + 2-acetoxyethyl acetoxymethyl ether (59278-00-1) → 2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one (75128-73-3)

Conditions	Yield
In methanol; toluene	91%

2-acetoxyethyl acetoxymethyl ether (59278-00-1) + acetic anhydride (108-24-7) + G (118-00-3) → 2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one (75128-73-3) + 7-<(2-acetoxyethoxy)methyl>-N2-acetylguanine (91702-60-2)

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 (59277-89-3) + acetic anhydride (108-24-7) → 9-[(acetoxyethoxy)methyl]guanine (102728-64-3) + 2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one (75128-73-3)

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 (160053-81-6) → 9-[(acetoxyethoxy)methyl]guanine (102728-64-3) + 9-<(2-acetoxyethoxy)methyl>-2-acetylamino-9H-purine (120356-09-4) + 2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one (75128-73-3)

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 (102728-64-3) → 2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one (75128-73-3)

Conditions	Yield
With dmap In hexane; acetic anhydride; toluene	79%

acycloguanosine (59277-89-3) + acetic anhydride (108-24-7) → 2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one (75128-73-3)

Conditions	Yield
With pyridine for 1h; Heating;	75%

2-hydroxyethyl acetate (542-59-6) + N9-methyl-N2-acetylguanine → 2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one (75128-73-3)

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 (19962-37-9) + 2-acetoxyethyl acetoxymethyl ether (59278-00-1) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → 2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one (75128-73-3)

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 (646-06-0) + acetic anhydride (108-24-7) + 2,9-diacetylguanine (3056-33-5) → 2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one (75128-73-3) + 7-<(2-acetoxyethoxy)methyl>-N2-acetylguanine (91702-60-2)

Conditions	Yield
With toluene-4-sulfonic acid; acetic acid In toluene at 120℃; for 2.5h;	A 29% B 29%

2-acetoxyethyl acetoxymethyl ether (59278-00-1) + toluene-4-sulfonic acid (104-15-4) + 7-<(2-acetoxyethoxy)methyl>-N2-acetylguanine (91702-60-2) → 2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one (75128-73-3) + 7,9-bis[(2-acetoxyethoxy)methyl]-N2-acetylguanine

Conditions	Yield
In chlorobenzene at 130℃; Substitution;	A 28% B 8%

Acetic acid 2-(2-oxo-propoxy)-ethyl ester (102728-65-4) + 2,9-diacetylguanine (3056-33-5) → 2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one (75128-73-3) + 7-<(2-acetoxyethoxy)methyl>-N2-acetylguanine (91702-60-2)

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 (59278-00-1) + G (118-00-3) → 2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one (75128-73-3) + 7-<(2-acetoxyethoxy)methyl>-N2-acetylguanine (91702-60-2)

Conditions	Yield
With acetic anhydride; toluene-4-sulfonic acid at 100℃; for 20h;	A 22% B 20%

1,3-DIOXOLANE (646-06-0) + 2,9-diacetylguanine (3056-33-5) → 2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one (75128-73-3) + 7-<(2-acetoxyethoxy)methyl>-N2-acetylguanine (91702-60-2)

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 (73-40-5) + 2-acetoxyethyl acetoxymethyl ether (59278-00-1) + acetic anhydride (108-24-7) → 2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one (75128-73-3) + 7-<(2-acetoxyethoxy)methyl>-N2-acetylguanine (91702-60-2)

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 (109-86-4) + acetic anhydride (108-24-7) + 2,9-diacetylguanine (3056-33-5) → 2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one (75128-73-3) + 7-<(2-acetoxyethoxy)methyl>-N2-acetylguanine (91702-60-2)

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 (160053-80-5) → 9-[(acetoxyethoxy)methyl]guanine (102728-64-3) + 9-<(2-acetoxyethoxy)methyl>-2-acetylamino-9H-purine (120356-09-4) + 2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one (75128-73-3) + 2-acetylamino-9-<(2-hydroxyethoxy)methyl>-9H-purine

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 (160053-81-6) → 9-<(2-acetoxyethoxy)methyl>-2-amino-9H-purine (92924-35-1) + 9-[(acetoxyethoxy)methyl]guanine (102728-64-3) + 2-acetylamino-9-<(2-hydroxyethoxy)methyl>-1,9-dihydro-6H-purin-6-one (110104-37-5) + 9-<(2-acetoxyethoxy)methyl>-2-acetylamino-9H-purine (120356-09-4) + 2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one (75128-73-3) + 2-acetylamino-9-<(2-hydroxyethoxy)methyl>-9H-purine

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 (160053-81-6) → 2-acetylamino-9-<(2-hydroxyethoxy)methyl>-1,9-dihydro-6H-purin-6-one (110104-37-5) + 9-<(2-acetoxyethoxy)methyl>-2-acetylamino-9H-purine (120356-09-4) + 2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one (75128-73-3) + 2-acetylamino-9-<(2-hydroxyethoxy)methyl>-9H-purine

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 (160053-79-2) → 9-[(acetoxyethoxy)methyl]guanine (102728-64-3) + 9-<(2-acetoxyethoxy)methyl>-2-acetylamino-9H-purine (120356-09-4) + 2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one (75128-73-3) + 2-acetylamino-9-<(2-hydroxyethoxy)methyl>-9H-purine

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 (30747-23-0) + 2-acetoxyethyl acetoxymethyl ether (59278-00-1) → 2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one (75128-73-3) + 7-<(2-acetoxyethoxy)methyl>-N2-acetylguanine (91702-60-2)

Conditions	Yield
With toluene-4-sulfonic acid at 100℃; for 48h;	A 42 % Chromat. B 30 % Chromat.

7-<(2-acetoxyethoxy)methyl>-N2-acetylguanine (91702-60-2) → 2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one (75128-73-3)

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 (30747-23-0) + 2-acetoxyethyl acetoxymethyl ether (59278-00-1) → 7-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-N2-acetylguanine (30747-22-9) + 2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one (75128-73-3) + 7-<(2-acetoxyethoxy)methyl>-N2-acetylguanine (91702-60-2)

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 (30747-22-9) + 2-acetoxyethyl acetoxymethyl ether (59278-00-1) → 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 (30747-23-0) + 2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one (75128-73-3) + 7-<(2-acetoxyethoxy)methyl>-N2-acetylguanine (91702-60-2)

Conditions	Yield
With toluene-4-sulfonic acid In chlorobenzene; acetonitrile at 120℃; for 2h;

7,9-bis[(2-acetoxyethoxy)methyl]-N2-acetylguanine → 2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one (75128-73-3) + 7-<(2-acetoxyethoxy)methyl>-N2-acetylguanine (91702-60-2)

Conditions	Yield
at 210℃; for 0.0833333h; Decomposition;
In chlorobenzene at 70℃; for 2h; Decomposition;

2-amino-1,9-dihydro-6H-purin-6-one (73-40-5) → 2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one (75128-73-3)

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 (364634-35-5) → 2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one (75128-73-3)

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 (75128-73-3) → acycloguanosine (59277-89-3)

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 (75128-73-3) → 9-[(acetoxyethoxy)methyl]guanine (102728-64-3)

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 (6553-96-4) + 2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one (75128-73-3) → 9-<(2-acetoxyethoxy)methyl>-2-acetylamino-6-(2,4,6-triisopropylbenzenesulfonyloxy)-9H-purine (160053-78-1)

Conditions	Yield
With dmap; triethylamine In dichloromethane Ambient temperature;	95%

ammonium hydroxide (1336-21-6) + 2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one (75128-73-3) → acycloguanosine (59277-89-3)

Conditions	Yield
In methanol	90%

2-mesitylenesulphonyl chloride (773-64-8) + 2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one (75128-73-3) → 9-<(2-acetoxyethoxy)methyl>-2-acetylamino-6-(2,4,6-trimethylbenzenesulfonyloxy)-9H-purine (160053-79-2)

Conditions	Yield
With dmap; triethylamine In dichloromethane for 1h; Ambient temperature;	81%

potassium tetrachloroplatinate(II) (10025-99-7) + 2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one (75128-73-3) → C24H30Cl2N10O10Pt (136686-48-1, 174173-25-2)

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 (75128-73-3) + diphenylcarbamic chloride (83-01-2) → 9-<(2-acetoxyethoxy)methyl>-2-N-acetyl-6-O-(diphenylcarbamoyl)guanine (112233-78-0)

Conditions	Yield
With pyridine; N-ethyl-N,N-diisopropylamine at 20℃; for 4h;	77%

2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one (75128-73-3) + p-toluenesulfonyl chloride (98-59-9) → 9-<(2-acetoxyethoxy)methyl>-2-acetylamino-6-(p-toluenesulfonyloxy)-9H-purine (160053-80-5)

Conditions	Yield
With dmap; triethylamine In dichloromethane for 10h; Ambient temperature;	74%

2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one (75128-73-3) → 2-((2-acetamido-6-thioxo-1,6-dihydro-9H-purin-9-yl)methoxy)ethyl acetate (92924-39-5)

Conditions	Yield
With [p-CH3OC6H4P(S)S]2 In pyridine for 7h; Heating;	74%
With diphosphorus pentasulfide In pyridine	65%

4-Fluorobenzenesulfonyl chloride (349-88-2) + 2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one (75128-73-3) → 9-<(2-acetoxyethoxy)methyl>-2-acetylamino-6-(p-fluorobenzenesulfonyloxy)-9H-purine (160053-81-6)

Conditions	Yield
With dmap; triethylamine In dichloromethane for 24h; Ambient temperature;	70%

potassium trichloro(ethene)platinate(II) (12012-50-9) + 2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one (75128-73-3) → trans-{PtCl2(η(2)-C2H4)(9-(2-acetoxyethoxymethyl)-N(2)-acetylguanine)} (136686-43-6)

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 (75128-73-3) → 2-acetylamino-9-<(2-hydroxyethoxy)methyl>-1,9-dihydro-6H-purin-6-one (110104-37-5)

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) (15274-33-6) + 2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one (75128-73-3) → trans-(PtCl2(DMSO)(9-(2-acetoxyethoxymethyl)-N(2)-acetylguanine)) (136686-46-9, 136778-46-6) + cis-(PtCl2(DMSO)(9-(2-acetoxyethoxymethyl)-N(2)-acetylguanine)) (136686-46-9, 136778-46-6)

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 (75128-73-3) + benzyl bromide (100-39-0) → 2-Acetamido-9-[(2-acetoxyethoxy)methyl]-6-benzyloxypurine + 9-[(2-Acetoxyethoxy)methyl]-2-(N-benzylacetamido)-6-benzyloxypurine

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 (75128-73-3) → 9-<(2-acetoxyethoxy)methyl>-2-acetylamino-6-chloro-9H-purine (120356-08-3)

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 (75128-73-3) + methyl iodide (74-88-4) → 9-[(2-Acetoxyethoxy)methyl]-6-methoxy-2-(N-methylacetamido)purine + 2-Acetamido-9-[(2-acetoxyethoxy)methyl]-6-methoxypurine + 9-[(2-Acetoxyethoxy)methyl]-1-methyl-2-(N-methylacetamido)-6-oxopurine

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 (75128-73-3) → Acetic acid 2-(2-acetylamino-8-fluoro-6-oxo-1,6-dihydro-purin-9-ylmethoxy)-ethyl ester

Conditions	Yield
With fluorine In chloroform for 1h; Ambient temperature;	30%

Upstream product

• 73-40-5 2-amino-1,9-dihydro-6H-purin-6-one 
• 59278-00-1 2-acetoxyethyl acetoxymethyl ether 
• 108-24-7 acetic anhydride 
• 109-86-4 2-methoxy-ethanol 
• 3056-33-5 2,9-diacetylguanine 
• 30747-23-0 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 
• 646-06-0 1,3-DIOXOLANE 
• 19962-37-9 N-(6-oxo-6,9-dihydro-1H-purin-2-yl)acetamide 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 542-59-6 2-hydroxyethyl acetate 
• 102728-64-3 9-[(acetoxyethoxy)methyl]guanine 
• 364634-35-5 9-(2-trimethylsilyloxyethoxymethyl)guanine 
• 118-00-3 G 
• 59277-89-3 acycloguanosine 

Downstream Products

• 112233-78-0 9-<(2-acetoxyethoxy)methyl>-2-N-acetyl-6-O-(diphenylcarbamoyl)guanine 
• 81777-48-2 9-<(2-acetoxyethoxy)methyl>-2-amino-6-chloro-9H-purine 
• 84408-37-7 deoxyacyclovir 
• 81777-49-3 2-amino-6-chloro-9-<(2-hydroxyethoxy)methyl>-9H-purine 
• 364634-52-6 pentanedioic acid 2-(2-amino-6-oxo-1,6-dihydro-purin-9-ylmethoxy)-ethyl ester benzyl ester 
• 364634-45-7 benzyloxycarbonylamino-acetic acid 2-(2-amino-6-oxo-1,6-dihydro-purin-9-ylmethoxy)-ethyl ester 
• 160053-80-5 9-<(2-acetoxyethoxy)methyl>-2-acetylamino-6-(p-toluenesulfonyloxy)-9H-purine 
• 110104-37-5 2-acetylamino-9-<(2-hydroxyethoxy)methyl>-1,9-dihydro-6H-purin-6-one 
• 102728-64-3 9-[(acetoxyethoxy)methyl]guanine 
• 59277-89-3 acycloguanosine 
• 160053-81-6 9-<(2-acetoxyethoxy)methyl>-2-acetylamino-6-(p-fluorobenzenesulfonyloxy)-9H-purine 
• 160053-78-1 9-<(2-acetoxyethoxy)methyl>-2-acetylamino-6-(2,4,6-triisopropylbenzenesulfonyloxy)-9H-purine 
• 160053-79-2 9-<(2-acetoxyethoxy)methyl>-2-acetylamino-6-(2,4,6-trimethylbenzenesulfonyloxy)-9H-purine 

Relevant articles and documents

Structure and properties of 7,9-diglycosylguanine - An unstable intermediate in transglycosylation of guanine nucleosides

7,9-bis[(2-Acetoxyethoxy)methyl]-N2-acetylguanine (1), an unstable intermediate in the 7→9 transglycosylation of acyclovir, has been isolated and characterized by spectroscopy and chemical degradation.

Method for synthesizing acyclovir and ganciclovir by carbon-hydrogen bond activation

The invention discloses a method for synthesizing acyclovir and ganciclovir by carbon-hydrogen bond activation and belongs to the field of organic synthesis. The method comprises that inexpensive guanine as a raw material undergoes methyl protection on 9th NH, a high-valent iodine reagent and monoacetyl-protected ethylene glycol or 1, 2-isopropylidene-protected glycerol are added into the raw material under catalysis of palladium acetate, the mixture undergo a heating reaction to produce acetyl-protected acyclovir or acetyl-protected ganciclovir, and the acetyl group is removed by an inorganicalkali alcohol solution so that acyclovir and ganciclovir are obtained. The method utilizes cheap and easily available raw materials, prevents use risk and corrosive reagents, has the advantages of short reaction route, simple operation, high atomic economy and high total product yield, provides a novel synthesis route of acyclovir and ganciclovir and has a potential application prospect.

Engineering a selective small-molecule substrate binding site into a deoxyribozyme

A small goal: An RNA ligase deoxyribozyme is engineered to accept a small-molecule NTP substrate in a multiple-turnover fashion. Selective binding is enforced by hydrogen bonding, and structural preorganization within the NTP itself is important for its efficient utilization as a substrate. This study points the way toward a broader use of small-molecule substrates with nucleic acid enzymes. (Figure Presented)