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75128-73-3

Basic Information
CAS No.: 75128-73-3
Name: 9-[(2-Acetoxyethoxy)methyl]-N2-acetylguanine
Article Data: 22
Molecular Structure:
Molecular Structure of 75128-73-3 (9-[(2-Acetoxyethoxy)methyl]-N2-acetylguanine)
Formula: C12H15N5O5
Molecular Weight: 309.282
Synonyms: 9-[(2-Acetoxyethoxy)methyl]-N2-acetylguanine;N2-Acetyl-9-(2-acetoxyethoxymethyl)guanine;2,9-diacetylacyclovir;2-{[2-(acetylamino)-6-oxo-3,6-dihydro-9H-purin-9-yl]methoxy}ethyl acetate;9-[(2-Acetoxyethoxy)methyl]-acetylguanine;acetamide, N-[9-[[2-(acetyloxy)ethoxy]methyl]-6,9-dihydro-6-oxo-1H-purin-2-yl]-;
EINECS: 278-077-7
Density: 1.53 g/cm3
Melting Point: 204 °C
Appearance: white to light yellow crystal powder
Hazard Symbols: Xn,Xi
Risk Codes: 20/21/22-36/37/38
Safety: 26-36-37/39
PSA: 128.20000
LogP: -0.31180
Synthetic route
59278-00-1

2-acetoxyethyl acetoxymethyl ether

3056-33-5

2,9-diacetylguanine

75128-73-3

2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one

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

diacetyl guanine

59278-00-1

2-acetoxyethyl acetoxymethyl ether

75128-73-3

2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one

Conditions
ConditionsYield
In methanol; dichloromethane94%

diacetylguanine

diacetyl guanine

59278-00-1

2-acetoxyethyl acetoxymethyl ether

75128-73-3

2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one

Conditions
ConditionsYield
In methanol; toluene91%
59278-00-1

2-acetoxyethyl acetoxymethyl ether

108-24-7

acetic anhydride

A

75128-73-3

2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one

B

91702-60-2

7-<(2-acetoxyethoxy)methyl>-N2-acetylguanine

Conditions
ConditionsYield
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.
59277-89-3

acycloguanosine

108-24-7

acetic anhydride

A

102728-64-3

9-[(acetoxyethoxy)methyl]guanine

B

75128-73-3

2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one

Conditions
ConditionsYield
With dmap In N,N-dimethyl-formamide Acetylation;A 84%
B 4%
160053-81-6

9-<(2-acetoxyethoxy)methyl>-2-acetylamino-6-(p-fluorobenzenesulfonyloxy)-9H-purine

A

102728-64-3

9-[(acetoxyethoxy)methyl]guanine

B

120356-09-4

9-<(2-acetoxyethoxy)methyl>-2-acetylamino-9H-purine

C

75128-73-3

2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one

Conditions
ConditionsYield
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%
102728-64-3

9-[(acetoxyethoxy)methyl]guanine

75128-73-3

2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one

Conditions
ConditionsYield
With dmap In hexane; acetic anhydride; toluene79%
59277-89-3

acycloguanosine

108-24-7

acetic anhydride

75128-73-3

2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one

Conditions
ConditionsYield
With pyridine for 1h; Heating;75%
542-59-6

2-hydroxyethyl acetate

N9-methyl-N2-acetylguanine

75128-73-3

2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one

Conditions
ConditionsYield
With bis(tertbutylcarbonyloxy)iodobenzene; palladium diacetate In toluene at 90℃; for 24h;70%
19962-37-9

N-(6-oxo-6,9-dihydro-1H-purin-2-yl)acetamide

59278-00-1

2-acetoxyethyl acetoxymethyl ether

999-97-3

1,1,1,3,3,3-hexamethyl-disilazane

75128-73-3

2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one

Conditions
ConditionsYield
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%
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Specification

The Acetamide,N-[9-[[2-(acetyloxy)ethoxy]methyl]-6,9-dihydro-6-oxo-1H-purin-2-yl]-, with the CAS registry number 75128-73-3 and EINECS registry number 278-077-7, is a kind of white to light yellow crystal powder, and belongs to the following product categories: Active Pharmaceutical Ingredients; Heterocyclic Compounds; Heterocycles; Impurities; Intermediates & Fine Chemicals; Pharmaceuticals. And the molecular formula of the chemical is C12H15N5O5. It is always used as intermediates of acyclovir.

The physical properties of Acetamide,N-[9-[[2-(acetyloxy)ethoxy]methyl]-6,9-dihydro-6-oxo-1H-purin-2-yl]- are as followings: (1)# of Rule of 5 Violations: 1; (2)ACD/LogD (pH 5.5): -0.75; (3)ACD/LogD (pH 7.4): -0.77; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 10; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 6; (11)Polar Surface Area: 106.33 Å2; (12)Index of Refraction: 1.654; (13)Molar Refractivity: 73.88 cm3; (14)Molar Volume: 201.5 cm3; (15)Polarizability: 29.29×10-24cm3; (16)Surface Tension: 60.2 dyne/cm; (17)Density: 1.53 g/cm3.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(NC/1=N/C(=O)c2ncn(c2N\1)COCCOC(=O)C)C
(2)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)
(3)InChIKey: VBHLKZHSCMQLTI-UHFFFAOYAF