Product Name

  • Name

    Ganciclovir

  • EINECS 627-054-3
  • CAS No. 82410-32-0
  • Article Data36
  • CAS DataBase
  • Density 1.81 g/cm3
  • Solubility 0.1 M HCl: 10 mg/mL
  • Melting Point 250 °C
  • Formula C9H13N5O4
  • Boiling Point 675 °C at 760 mmHg
  • Molecular Weight 255.233
  • Flash Point 362 °C
  • Transport Information
  • Appearance white powder
  • Safety 53-36/37/39-45
  • Risk Codes 46-60-61
  • Molecular Structure Molecular Structure of 82410-32-0 (Ganciclovir)
  • Hazard Symbols ToxicT
  • Synonyms Gancyclovir;
  • PSA 139.28000
  • LogP -1.38970

Synthetic route

N2-acetyl-9-(1,3-dihydroxy-2-propoxymethyl)guanine
84960-04-3

N2-acetyl-9-(1,3-dihydroxy-2-propoxymethyl)guanine

ganciclovir
82410-32-0

ganciclovir

Conditions
ConditionsYield
With ammonium hydroxide In methanol at 20℃; for 17h;94%
With ammonium hydroxide In methanol at 25℃; for 16h; Yield given;
9-(1,3-diacetoxy-2-propoxymethyl)-N2-acetylguanine
86357-14-4

9-(1,3-diacetoxy-2-propoxymethyl)-N2-acetylguanine

ganciclovir
82410-32-0

ganciclovir

Conditions
ConditionsYield
With ammonium hydroxide for 72h; Ambient temperature;91%
With acetic acid In water; methylamine87%
With potassium hydroxide at 70℃; for 0.5h; Reagent/catalyst; Microwave irradiation;82.8%
With methanol; potassium hydroxide at 20℃; for 12h;78%
With acetic acid In methylamine
9-<<2-(benzyloxy)-1-<(benzyloxy)methyl>ethoxy>methyl>guanine
82410-31-9

9-<<2-(benzyloxy)-1-<(benzyloxy)methyl>ethoxy>methyl>guanine

ganciclovir
82410-32-0

ganciclovir

Conditions
ConditionsYield
palladium dichloride In ethanol; cyclohexene for 5h; Heating;90%
With palladium; cyclohexene In ethanol87.7%
With cyclohexene; palladium In ethanol for 24h; Heating;87.7%
With cyclohexene; palladium In ethanol
9-<<2-benzyloxy-1-(benzyloxymethyl)ethoxy>methyl>guanine
82410-31-9

9-<<2-benzyloxy-1-(benzyloxymethyl)ethoxy>methyl>guanine

ganciclovir
82410-32-0

ganciclovir

Conditions
ConditionsYield
With ethanol; palladium In cyclohexene for 18h; Heating;84%
N2-acetyl-9-((1,3-pivaloyloxy-2-propoxy)methyl)guanine
100675-29-4

N2-acetyl-9-((1,3-pivaloyloxy-2-propoxy)methyl)guanine

ganciclovir
82410-32-0

ganciclovir

Conditions
ConditionsYield
With sodium methylate In methanol for 40h; Heating;72%
1-<(1,3-dihydroxy-2-propoxy)methyl>-5-<(thiocarbamoyl)amino>-1H-imidazole-4-carboxamide
131490-72-7

1-<(1,3-dihydroxy-2-propoxy)methyl>-5-<(thiocarbamoyl)amino>-1H-imidazole-4-carboxamide

ganciclovir
82410-32-0

ganciclovir

Conditions
ConditionsYield
With sodium hydroxide; copper(II) sulfate for 1h; Heating;61%
2-(2-amino-1,6-dihydro-6-oxopurin-9-yl)methoxy-1,3-bis-1'-propyl-(2'S)-azido-3'-methylbutanoate
1219792-39-8

2-(2-amino-1,6-dihydro-6-oxopurin-9-yl)methoxy-1,3-bis-1'-propyl-(2'S)-azido-3'-methylbutanoate

A

2-[(2-amino-1,6-dihydro-6-oxopurin-9-yl)methyloxy]-3-hydroxypropyl 2'-(S)-azido-3'-methylbutanoate
1219792-38-7

2-[(2-amino-1,6-dihydro-6-oxopurin-9-yl)methyloxy]-3-hydroxypropyl 2'-(S)-azido-3'-methylbutanoate

B

ganciclovir
82410-32-0

ganciclovir

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In methanol at 20℃; for 14h;A 34.5%
B 20 %Chromat.
C23H21N5O6
86629-51-8

C23H21N5O6

ganciclovir
82410-32-0

ganciclovir

Conditions
ConditionsYield
With ammonia In methanol Yield given;
9-<<2-hydroxy-1-(hydroxymethyl)ethoxy>methyl>-2,6-diamino-purine
86629-59-6

9-<<2-hydroxy-1-(hydroxymethyl)ethoxy>methyl>-2,6-diamino-purine

ganciclovir
82410-32-0

ganciclovir

Conditions
ConditionsYield
at 25℃; for 18h; adenosine deaminase, pH = 7.5;
9-<(1-acetoxy-2-hydroxymethyl)ethoxymethyl>guanine
88110-89-8

9-<(1-acetoxy-2-hydroxymethyl)ethoxymethyl>guanine

A

ganciclovir
82410-32-0

ganciclovir

B

acetic acid
64-19-7

acetic acid

Conditions
ConditionsYield
With New Zealand albino male rabbit cornea homogenate In phosphate buffer at 37℃; for 24h; Kinetics; Further Variations:; Reagents;
ganciclovir dipropionate

ganciclovir dipropionate

A

ganciclovir
82410-32-0

ganciclovir

B

propionic acid
802294-64-0

propionic acid

Conditions
ConditionsYield
With New Zealand albino male rabbit cornea homogenate In phosphate buffer at 37℃; for 24h; Kinetics; Further Variations:; Reagents;
9-(1,3-diacetoxy-2-propoxymethyl)guanine
86357-19-9

9-(1,3-diacetoxy-2-propoxymethyl)guanine

A

ganciclovir
82410-32-0

ganciclovir

B

acetic acid
64-19-7

acetic acid

Conditions
ConditionsYield
With New Zealand albino male rabbit cornea homogenate In phosphate buffer at 37℃; for 24h; Kinetics; Further Variations:; Reagents;
ganciclovir dibutyrate
88110-71-8

ganciclovir dibutyrate

A

ganciclovir
82410-32-0

ganciclovir

B

butyric acid
107-92-6

butyric acid

Conditions
ConditionsYield
With New Zealand albino male rabbit cornea homogenate In phosphate buffer at 37℃; for 24h; Kinetics; Further Variations:; Reagents;
ganciclovir monopropionate
194159-18-7

ganciclovir monopropionate

A

ganciclovir
82410-32-0

ganciclovir

B

propionic acid
802294-64-0

propionic acid

Conditions
ConditionsYield
With New Zealand albino male rabbit cornea homogenate In phosphate buffer at 37℃; for 24h; Kinetics; Further Variations:; Reagents;
ganciclovir diisobutyrate

ganciclovir diisobutyrate

A

ganciclovir
82410-32-0

ganciclovir

B

isobutyric Acid
79-31-2

isobutyric Acid

Conditions
ConditionsYield
With New Zealand albino male rabbit cornea homogenate In phosphate buffer at 37℃; for 24h; Kinetics; Further Variations:; Reagents;
ganciclovir monobutyrate
298197-24-7

ganciclovir monobutyrate

A

ganciclovir
82410-32-0

ganciclovir

B

butyric acid
107-92-6

butyric acid

Conditions
ConditionsYield
With New Zealand albino male rabbit cornea homogenate In phosphate buffer at 37℃; for 24h; Kinetics; Further Variations:; Reagents;
ganciclovir monovalerate

ganciclovir monovalerate

A

ganciclovir
82410-32-0

ganciclovir

B

valeric acid
109-52-4

valeric acid

Conditions
ConditionsYield
With New Zealand albino male rabbit cornea homogenate In phosphate buffer at 37℃; for 24h; Kinetics; Further Variations:; Reagents;
2-amino-1,9-dihydro-6H-purin-6-one
73-40-5

2-amino-1,9-dihydro-6H-purin-6-one

ganciclovir
82410-32-0

ganciclovir

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: (NH4)2SO4
2: Bu4NF / tetrahydrofuran
3: cyclohexene / Pd / ethanol
View Scheme
Multi-step reaction with 3 steps
1: ammonium sulfate / 96 h / Heating
2: 17.8 percent / tetrabutylammonium fluoride / tetrahydrofuran / 22 h / Heating
3: 87.7 percent / cyclohexene / palladium black / ethanol / 24 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: (NH4)2SO4
2: Bu4NF / tetrahydrofuran
3: 87.7 percent / Pd black; cyclohexene / ethanol
View Scheme
2,6,9-tris(trimethylsilyl)guanine
18602-85-2

2,6,9-tris(trimethylsilyl)guanine

ganciclovir
82410-32-0

ganciclovir

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Bu4NF / tetrahydrofuran
2: cyclohexene / Pd / ethanol
View Scheme
Multi-step reaction with 2 steps
1: 17.8 percent / tetrabutylammonium fluoride / tetrahydrofuran / 22 h / Heating
2: 87.7 percent / cyclohexene / palladium black / ethanol / 24 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: Bu4NF / tetrahydrofuran
2: 87.7 percent / Pd black; cyclohexene / ethanol
View Scheme
N2-acetyl-9-<<1,3-bis(benzyloxy)-2-propoxy>methyl>guanine
82410-30-8

N2-acetyl-9-<<1,3-bis(benzyloxy)-2-propoxy>methyl>guanine

ganciclovir
82410-32-0

ganciclovir

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 90 percent / EtOH / Pd(OH)2/C / cyclohexane / 40 h / Heating
2: 94 percent / aq. ammonium hydroxide / methanol / 17 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: 20percent Pd(OH)2/C / cyclohexene; ethanol / 32 h / Heating
2: 56percent NH4OH / methanol / 16 h / 25 °C
View Scheme
Multi-step reaction with 2 steps
1: 99 percent / conc. ammonium hydroxide, pyridine / 15 h / 55 °C
2: 84 percent / ethanol / palladium black / cyclohexene / 18 h / Heating
View Scheme
2,9-diacetylguanine
3056-33-5

2,9-diacetylguanine

ganciclovir
82410-32-0

ganciclovir

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 31 percent / p-toluenesulfonic acid / tetrahydrothiophene 1,1-dioxide / 85 h / 95 °C
2: 90 percent / EtOH / Pd(OH)2/C / cyclohexane / 40 h / Heating
3: 94 percent / aq. ammonium hydroxide / methanol / 17 h / 20 °C
View Scheme
7-(1,3-diacetoxy-2-propoxymethyl)-N2-acetylguanine
86357-17-7

7-(1,3-diacetoxy-2-propoxymethyl)-N2-acetylguanine

ganciclovir
82410-32-0

ganciclovir

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 50 percent / 0.17 h / 230 °C
2: 91 percent / NH4OH / 72 h / Ambient temperature
View Scheme
N-(6-oxo-6,9-dihydro-1H-purin-2-yl)acetamide
19962-37-9

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

ganciclovir
82410-32-0

ganciclovir

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) HMDS, ammonium sulfate; 2.) TBAI; 3.)methanol, water
2: 99 percent / conc. ammonium hydroxide, pyridine / 15 h / 55 °C
3: 84 percent / ethanol / palladium black / cyclohexene / 18 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: potassium carbonate / N,N-dimethyl-formamide / 8 h / 20 °C
2: palladium diacetate; bis(tertbutylcarbonyloxy)iodobenzene / toluene / 24 h / 120 °C
3: methanol; potassium hydroxide / 12 h / 20 °C
View Scheme
2,6-bisacetamidopurine
34097-37-5

2,6-bisacetamidopurine

ganciclovir
82410-32-0

ganciclovir

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 5.4 g / triethylamine / dimethylformamide / 1.) r.t. 60 h; 2.) 40 deg C, 1 h
2: 85 percent / Na / methanol / 1.) reflux, 2 h; 2.) r.t. 12 h
3: 80 percent / palladium oxide, cyclohexene / ethanol / 3 h / Heating
4: 18 h / 25 °C / adenosine deaminase, pH = 7.5
View Scheme
9-(2-Benzyloxy-1-benzyloxymethyl-ethoxymethyl)-9H-purine-2,6-diamine
89419-14-7

9-(2-Benzyloxy-1-benzyloxymethyl-ethoxymethyl)-9H-purine-2,6-diamine

ganciclovir
82410-32-0

ganciclovir

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 80 percent / palladium oxide, cyclohexene / ethanol / 3 h / Heating
2: 18 h / 25 °C / adenosine deaminase, pH = 7.5
View Scheme
N-[2-Acetylamino-9-(2-benzyloxy-1-benzyloxymethyl-ethoxymethyl)-9H-purin-6-yl]-acetamide
89419-13-6

N-[2-Acetylamino-9-(2-benzyloxy-1-benzyloxymethyl-ethoxymethyl)-9H-purin-6-yl]-acetamide

ganciclovir
82410-32-0

ganciclovir

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 85 percent / Na / methanol / 1.) reflux, 2 h; 2.) r.t. 12 h
2: 80 percent / palladium oxide, cyclohexene / ethanol / 3 h / Heating
3: 18 h / 25 °C / adenosine deaminase, pH = 7.5
View Scheme
9-<<2-benzyloxy-1-(benzyloxymethyl)ethoxy>-methyl>-6-chloroguanine
84222-47-9

9-<<2-benzyloxy-1-(benzyloxymethyl)ethoxy>-methyl>-6-chloroguanine

ganciclovir
82410-32-0

ganciclovir

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 70 percent / sodium, mercaptoethanol, water / methanol / 2.5 h / Heating
2: 84 percent / ethanol / palladium black / cyclohexene / 18 h / Heating
View Scheme
2-Amino-6-chloropurin
10310-21-1

2-Amino-6-chloropurin

ganciclovir
82410-32-0

ganciclovir

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) 1,1,1,3,3,3-hexamethyldisilazane, ammonium sulfate; 2.) mercuric cyanide / 1.) 2 h, reflux; 2.) benzene, 3 h, reflux
2: 70 percent / sodium, mercaptoethanol, water / methanol / 2.5 h / Heating
3: 84 percent / ethanol / palladium black / cyclohexene / 18 h / Heating
View Scheme
5-amino-1-<(1,3-dihydroxy-2-propoxy)methyl>-1H-imidazole-4-carboxamide
131490-62-5

5-amino-1-<(1,3-dihydroxy-2-propoxy)methyl>-1H-imidazole-4-carboxamide

ganciclovir
82410-32-0

ganciclovir

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 2) K2CO3 / 1) acetone, reflux, 1 h, 2) methanol, reflux, 4 h
2: 61 percent / 3N aq. NaOH, copper(II) sulfate / 1 h / Heating
View Scheme
ganciclovir
82410-32-0

ganciclovir

2-Methylpropionic anhydride
97-72-3

2-Methylpropionic anhydride

isobutyric acid 2-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-ylmethoxy)-3-isobutyryloxy-propyl ester

isobutyric acid 2-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-ylmethoxy)-3-isobutyryloxy-propyl ester

Conditions
ConditionsYield
With pyridine; dmap for 1h; Acylation; Heating;99%
ganciclovir
82410-32-0

ganciclovir

1-hexadecylcarboxylic acid
57-10-3

1-hexadecylcarboxylic acid

Hexadecanoic acid 2-(2-amino-6-oxo-1,6-dihydro-purin-9-ylmethoxy)-3-hexadecanoyloxy-propyl ester

Hexadecanoic acid 2-(2-amino-6-oxo-1,6-dihydro-purin-9-ylmethoxy)-3-hexadecanoyloxy-propyl ester

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 50℃; for 50h;97%
tert-butoxyphosphonic acid dichloride

tert-butoxyphosphonic acid dichloride

ganciclovir
82410-32-0

ganciclovir

C13H22N5O7P

C13H22N5O7P

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 50℃; for 5h; Inert atmosphere;96.8%
ganciclovir
82410-32-0

ganciclovir

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

9-<(1,3-bis(tert-butyldimethylsilyloxy)-2-propoxy)methyl>guanine
109082-88-4

9-<(1,3-bis(tert-butyldimethylsilyloxy)-2-propoxy)methyl>guanine

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide for 1h; Ambient temperature;95%
ganciclovir
82410-32-0

ganciclovir

C9H11Cl2N5O2

C9H11Cl2N5O2

Conditions
ConditionsYield
With phosphorus pentachloride In tetrahydrofuran at 0 - 10℃; for 1h;92.7%
ganciclovir
82410-32-0

ganciclovir

acetic anhydride
108-24-7

acetic anhydride

9-(1,3-diacetoxy-2-propoxymethyl)guanine
86357-19-9

9-(1,3-diacetoxy-2-propoxymethyl)guanine

Conditions
ConditionsYield
With dmap Ambient temperature;91%
With dmap In N,N-dimethyl-formamide at 23℃; Acetylation;90%
ganciclovir
82410-32-0

ganciclovir

tert-butylchlorodiphenylsilane
58479-61-1

tert-butylchlorodiphenylsilane

2-amino-9-[2-(tert-butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-ethoxymethyl]-1,9-dihydro-purin-6-one
266684-38-2

2-amino-9-[2-(tert-butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-ethoxymethyl]-1,9-dihydro-purin-6-one

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 24h; Substitution; silylation;91%
trimethyl orthovalerate
13820-09-2

trimethyl orthovalerate

ganciclovir
82410-32-0

ganciclovir

A

ganciclovir monovalerate

ganciclovir monovalerate

B

pentanoic acid 3-hydroxy-2-(6-oxo-2-pentanoylamino-1,6-dihydro-purin-9-ylmethoxy)-propyl ester

pentanoic acid 3-hydroxy-2-(6-oxo-2-pentanoylamino-1,6-dihydro-purin-9-ylmethoxy)-propyl ester

Conditions
ConditionsYield
Stage #1: trimethyl orthovalerate; ganciclovir With trifluoroacetic acid In N,N-dimethyl-formamide at 23℃; for 2h; Substitution;
Stage #2: With water In N,N-dimethyl-formamide at 23℃; Hydrolysis;
A 90%
B 5%
ganciclovir
82410-32-0

ganciclovir

azidovaline
40224-47-3

azidovaline

2-(2-amino-1,6-dihydro-6-oxopurin-9-yl)methoxy-1,3-bis-1'-propyl-(2'S)-azido-3'-methylbutanoate
1219792-39-8

2-(2-amino-1,6-dihydro-6-oxopurin-9-yl)methoxy-1,3-bis-1'-propyl-(2'S)-azido-3'-methylbutanoate

Conditions
ConditionsYield
Stage #1: ganciclovir With benzotriazol-1-ol; triethylamine In dimethyl sulfoxide at 25 - 30℃; for 0.166667h;
Stage #2: azidovaline In dimethyl sulfoxide at 25 - 30℃;
Stage #3: With dicyclohexyl-carbodiimide In dimethyl sulfoxide at 25 - 30℃; for 2h;
88.8%
Stage #1: ganciclovir With triethanolamine; benzotriazol-1-ol In dimethyl sulfoxide at 25 - 30℃;
Stage #2: azidovaline With dicyclohexyl-carbodiimide In dimethyl sulfoxide at 20 - 30℃;
ganciclovir
82410-32-0

ganciclovir

propionic acid anhydride
123-62-6

propionic acid anhydride

ganciclovir dipropionate

ganciclovir dipropionate

Conditions
ConditionsYield
With dmap In N,N-dimethyl-formamide at 23℃; Esterification;88%
With dmap Ambient temperature;52%
ganciclovir
82410-32-0

ganciclovir

1,1'-carbonyldiimidazole
530-62-1

1,1'-carbonyldiimidazole

9-<(1,3-di(imidazol-1-ylcarbonyloxy)-2-propoxy)methyl>guanine

9-<(1,3-di(imidazol-1-ylcarbonyloxy)-2-propoxy)methyl>guanine

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 50℃; for 18h;87%
trimethoxypropane
24823-81-2

trimethoxypropane

ganciclovir
82410-32-0

ganciclovir

A

ganciclovir monopropionate
194159-18-7

ganciclovir monopropionate

B

propionic acid 3-hydroxy-2-(6-oxo-2-propionylamino-1,6-dihydro-purin-9-ylmethoxy)-propyl ester

propionic acid 3-hydroxy-2-(6-oxo-2-propionylamino-1,6-dihydro-purin-9-ylmethoxy)-propyl ester

Conditions
ConditionsYield
Stage #1: trimethoxypropane; ganciclovir With trifluoroacetic acid In N,N-dimethyl-formamide at 23℃; for 2h; Substitution;
Stage #2: With water In N,N-dimethyl-formamide at 23℃; Hydrolysis;
A 87%
B 6%
butanoic acid anhydride
106-31-0

butanoic acid anhydride

ganciclovir
82410-32-0

ganciclovir

ganciclovir dibutyrate
88110-71-8

ganciclovir dibutyrate

Conditions
ConditionsYield
With dmap Ambient temperature;86%
With dmap In N,N-dimethyl-formamide at 23℃; Esterification;80%
ganciclovir
82410-32-0

ganciclovir

4-isobutyryloxyphenacyl bromide
476360-57-3

4-isobutyryloxyphenacyl bromide

isobutyric acid 4-[3-(2-hydroxy-1-hydroxymethyl-ethoxymethyl)-8-oxo-5,8-dihydro-3H-1,3,4,5,7a-pentaaza-s-indacen-6-yl]-phenyl ester
476360-70-0

isobutyric acid 4-[3-(2-hydroxy-1-hydroxymethyl-ethoxymethyl)-8-oxo-5,8-dihydro-3H-1,3,4,5,7a-pentaaza-s-indacen-6-yl]-phenyl ester

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide86%
Stage #1: ganciclovir With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h;
Stage #2: 4-isobutyryloxyphenacyl bromide In N,N-dimethyl-formamide at 20℃; for 4h; Further stages.;
55%
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 4h;
ganciclovir
82410-32-0

ganciclovir

2,2-dimethylpropanoic anhydride
1538-75-6

2,2-dimethylpropanoic anhydride

9-<(1,3-dipivaloyloxy-2-propoxy)methyl>guanine

9-<(1,3-dipivaloyloxy-2-propoxy)methyl>guanine

Conditions
ConditionsYield
With dmap In N,N-dimethyl-formamide for 48h; Ambient temperature;84%
ganciclovir
82410-32-0

ganciclovir

N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

N'-(9-{[(1,3-dihydroxypropan-2-yl)oxy]methyl}-6-oxo-6,9-dihydro-1H-purin-2-yl)-N,N-dimethylmethanimidamide

N'-(9-{[(1,3-dihydroxypropan-2-yl)oxy]methyl}-6-oxo-6,9-dihydro-1H-purin-2-yl)-N,N-dimethylmethanimidamide

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 29h;84%
1,1,1-trimethoxybutane
43083-12-1

1,1,1-trimethoxybutane

ganciclovir
82410-32-0

ganciclovir

A

ganciclovir monobutyrate
298197-24-7

ganciclovir monobutyrate

B

butyric acid 2-(2-butyrylamino-6-oxo-1,6-dihydro-purin-9-ylmethoxy)-3-hydroxy-propyl ester

butyric acid 2-(2-butyrylamino-6-oxo-1,6-dihydro-purin-9-ylmethoxy)-3-hydroxy-propyl ester

Conditions
ConditionsYield
Stage #1: 1,1,1-trimethoxybutane; ganciclovir With trifluoroacetic acid In N,N-dimethyl-formamide at 23℃; for 2h; Substitution;
Stage #2: With water In N,N-dimethyl-formamide at 23℃; Hydrolysis;
A 83%
B 15%
ganciclovir
82410-32-0

ganciclovir

N-(Benzyloxycarbonyl)glycine
1138-80-3

N-(Benzyloxycarbonyl)glycine

Benzyloxycarbonylamino-acetic acid 2-(2-amino-6-oxo-1,6-dihydro-purin-9-ylmethoxy)-3-(2-benzyloxycarbonylamino-acetoxy)-propyl ester

Benzyloxycarbonylamino-acetic acid 2-(2-amino-6-oxo-1,6-dihydro-purin-9-ylmethoxy)-3-(2-benzyloxycarbonylamino-acetoxy)-propyl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 48h; Acylation;81%
ganciclovir
82410-32-0

ganciclovir

2-Methylpropionic anhydride
97-72-3

2-Methylpropionic anhydride

ganciclovir diisobutyrate

ganciclovir diisobutyrate

Conditions
ConditionsYield
With dmap In N,N-dimethyl-formamide at 23℃; Esterification;80%
ganciclovir
82410-32-0

ganciclovir

acetic anhydride
108-24-7

acetic anhydride

9-(1,3-diacetoxy-2-propoxymethyl)-N2-acetylguanine
86357-14-4

9-(1,3-diacetoxy-2-propoxymethyl)-N2-acetylguanine

Conditions
ConditionsYield
With pyridine for 6h; Reflux;80%
undecylenic acid
112-37-8

undecylenic acid

ganciclovir
82410-32-0

ganciclovir

undecanoic acid 2-(2-amino-6-oxo-1,6-dihydro-purin-9-ylmethoxy)-3-undecanoyloxy-propyl ester

undecanoic acid 2-(2-amino-6-oxo-1,6-dihydro-purin-9-ylmethoxy)-3-undecanoyloxy-propyl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 23℃; for 48h; Esterification;78%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

ganciclovir
82410-32-0

ganciclovir

2-amino-9-((2-phenyl-1,3-dioxan-5-yloxy)methyl)-1H-purin-6(9H)-one

2-amino-9-((2-phenyl-1,3-dioxan-5-yloxy)methyl)-1H-purin-6(9H)-one

Conditions
ConditionsYield
Stage #1: benzaldehyde dimethyl acetal; ganciclovir With toluene-4-sulfonic acid In dimethyl sulfoxide at 25 - 80℃;
Stage #2: With triethylamine In water; dimethyl sulfoxide; ethyl acetate at 25 - 35℃;
78%
Isovaleric anhydride
1468-39-9

Isovaleric anhydride

ganciclovir
82410-32-0

ganciclovir

2-N-isobutyryl-9-{[(1,3-dihydroxypropan-2-yl)oxy]methyl}guanine

2-N-isobutyryl-9-{[(1,3-dihydroxypropan-2-yl)oxy]methyl}guanine

Conditions
ConditionsYield
Stage #1: ganciclovir With pyridine; chloro-trimethyl-silane at 20℃; for 0.25h;
Stage #2: Isovaleric anhydride at 20℃; for 3h;
Stage #3: With ammonia In water
76.8%
N-Acetylimidazole
2466-76-4

N-Acetylimidazole

ganciclovir
82410-32-0

ganciclovir

9-<(1-acetoxy-2-hydroxymethyl)ethoxymethyl>guanine
88110-89-8

9-<(1-acetoxy-2-hydroxymethyl)ethoxymethyl>guanine

Conditions
ConditionsYield
Stage #1: ganciclovir With Trimethyl borate In toluene for 5h; Reflux; Large scale;
Stage #2: N-Acetylimidazole With triethylamine at 20℃; for 6h; Large scale;
Stage #3: In methanol at 0 - 20℃; for 2h; Reagent/catalyst; Solvent; Large scale;
75.7%
Stage #1: ganciclovir With Trimethyl borate In toluene for 5h; Reflux;
Stage #2: N-Acetylimidazole With triethylamine In toluene at 20℃; for 6h;
Stage #3: With methanol In toluene at 0 - 20℃; for 2h; Reagent/catalyst; Solvent;
75.7%
Stage #1: ganciclovir With Trimethyl borate In toluene for 5h; Reflux;
Stage #2: N-Acetylimidazole With triethylamine In toluene at 20℃; for 6h;
Stage #3: With methanol In toluene at 0 - 20℃; for 2h; Reagent/catalyst; Solvent;
75.7%
Stage #1: ganciclovir With Trimethyl borate In toluene for 5h; Reflux;
Stage #2: N-Acetylimidazole With triethylamine In toluene at 20℃; for 6h; Reagent/catalyst; Solvent;
75.7%
vinyl acetate
108-05-4

vinyl acetate

ganciclovir
82410-32-0

ganciclovir

9-<(1-acetoxy-2-hydroxymethyl)ethoxymethyl>guanine
88110-89-8

9-<(1-acetoxy-2-hydroxymethyl)ethoxymethyl>guanine

Conditions
ConditionsYield
Stage #1: ganciclovir With triethyl borate In 2-methyltetrahydrofuran for 3h; Reflux; Large scale;
Stage #2: vinyl acetate With triethylamine at 20℃; for 6h; Large scale;
Stage #3: In ethanol at 0 - 20℃; for 3h; Reagent/catalyst; Solvent; Large scale;
75.2%
Stage #1: ganciclovir With triethyl borate In 2-methyltetrahydrofuran for 3h; Reflux;
Stage #2: vinyl acetate With triethylamine In 2-methyltetrahydrofuran at 20℃; for 6h;
Stage #3: With ethanol In 2-methyltetrahydrofuran at 0 - 20℃; for 2h; Reagent/catalyst; Solvent;
75.2%
Stage #1: ganciclovir With triethyl borate In 2-methyltetrahydrofuran for 3h; Reflux;
Stage #2: vinyl acetate With triethylamine In tetrahydrofuran at 20℃; for 6h;
Stage #3: With ethanol In tetrahydrofuran at 0 - 20℃; for 3h; Reagent/catalyst; Solvent;
75.2%
Stage #1: ganciclovir With triethyl borate In 2-methyltetrahydrofuran for 3h; Reflux;
Stage #2: vinyl acetate With triethylamine In 2-methyltetrahydrofuran at 20℃; for 6h; Reagent/catalyst; Solvent;
75.2%

Ganciclovir Specification

1. Introduction of Ganciclovir

Ganciclovir, with the IUPAC Name of 2-Amino-9-(1,3-dihydroxypropan-2-yloxymethyl)-3H-purin-6-one, is one kind of white powder. This chemical has the Classification Code which include Anti-Infective Agents; Antiviral; Antiviral agents; Drug / Therapeutic Agent; Mutation data. Besides, it belongs to the Product Categories which include Bases & Related Reagents; Intermediates & Fine Chemicals; Nucleotides; Pharmaceuticals; API's; Antiviral.

2. Properties of Ganciclovir

Ganciclovir has the following properties: (1)Index of Refraction: 1.76; (2)Molar Refractivity: 57.9 cm3; (3)Molar Volume: 140.5 cm3; (4)Polarizability: 22.95×10-24 cm3; (5)Surface Tension: 86.6 dyne/cm; (6)Density: 1.81 g/cm3; (7)Flash Point: 362 °C; (8)Enthalpy of Vaporization: 104.13 kJ/mol; (9)Boiling Point: 675 °C at 760 mmHg; (10)Melting Point: 250 °C; (11)storage temperature: 2-8 °C; (12)solubility: 0.1 M HCl: 10 mg/mL; (13)Vapour Pressure: 3.82E-19 mmHg at 25 °C.

3. Structure Descriptors of Ganciclovir

You could convert the following datas into the molecular structure:
(1).Canonical SMILES: c12c(ncn1COC(CO)CO)c([nH]c(n2)N)=O
(2).InChI: InChI=1/C9H13N5O4/c10-9-12-7-6(8(17)13-9)11-3-14(7)4-18-5(1-15)2-16/h3,5,15-16H,1-2,4H2,(H3,10,12,13,17)

4. Toxicity of Ganciclovir

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous > 150mg/kg (150mg/kg)   Drugs in Japan Vol. -, Pg. 291, 1990.
dog LD50 oral > 1gm/kg (1000mg/kg)   Drugs in Japan Vol. -, Pg. 291, 1990.
mouse LD50 intraperitoneal 1gm/kg (1000mg/kg)   Journal of Medicinal Chemistry. Vol. 26, Pg. 759, 1983.
mouse LD50 intravenous 900mg/kg (900mg/kg)   Drugs in Japan Vol. -, Pg. 291, 1990.
mouse LD50 oral > 2gm/kg (2000mg/kg)   Drugs in Japan Vol. -, Pg. 291, 1990.

5. Safety Information of Ganciclovir

Common adverse drug reactions >=1% of patients) include: neutropenia, granulocytopenia, thrombocytopenia, fever, nausea, vomiting, dyspepsia, diarrhoea, abdominal pain, flatulence, anorexia, raised liver enzymes, headache, confusion, hallucination, anaemia, pain and phlebitis at injection site (due to high pH), sweating, rash.
Hazard Codes: ToxicT
Risk Statements: 46-60-61 
R46:May cause heritable genetic damage. 
R60:May impair fertility. 
R61:May cause harm to the unborn child.
Safety Statements: 53-36/37/39-45 
S53:Avoid exposure - obtain special instructions before use. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
WGK Germany: 3
RTECS of Ganciclovir (CAS NO.82410-32-0): MF8407000

6. Use of Ganciclovir

Ganciclovir (CAS NO.82410-32-0) is an antiviral medication used to treat or prevent cytomegalovirus (CMV) infections.

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