Famciclovir supplier | CasNO.104227-87-4

Name
Famciclovir
EINECS 630-411-6
CAS No. 104227-87-4
Article Data31
CAS DataBase
Density 1.4 g/cm³
Solubility
Melting Point 102-104 °C
Formula C₁₄H₁₉N₅O₄
Boiling Point 550.2 °C at 760 mmHg
Molecular Weight 321.336
Flash Point 286.6 °C
Transport Information
Appearance off-white powder
Safety 36/37/39-45-53
Risk Codes 20/21/22-45-61
Molecular Structure
Hazard Symbols T
Synonyms Amciclovir;BRL 42810;[2-(acetyloxymethyl)-4-(2-aminopurin-9-yl)butyl] acetate;FCV;1,3-Propanediol, 2-(2-(2-amino-9H-purin-9-yl)ethyl)-, diacetate (ester);2-(2-(2-Amino-9H-purin-9-yl)ethyl)-1,3-propanediol diacetate (ester);Diacetyl 6-deoxy-9-(4-hydroxy-3-hydroxymethyl-but-1-yl)guanine;Famvir;1,3-Propanediol,2-[2-(2-amino-9H-purin-9- yl)ethyl]-,diacetate (ester);Butenafine Hydrochloride;Famcyclovir;
PSA 122.22000
LogP 1.12220

Synthetic route

: 108-24-7
acetic anhydride

: 104227-86-3
6-deoxypenciclovir

: 104227-87-4
9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine

Conditions

Conditions	Yield
With pyridine; dmap In tetrahydrofuran at 20℃; for 3h;	97%
With triethylamine In dichloromethane at 20 - 30℃; for 10h;	90%
With pyridine; dmap In tetrahydrofuran for 3h; Ambient temperature;	74%
Stage #1: 6-deoxypenciclovir With hydrogenchloride In water at 45 - 50℃; for 1.5h; Stage #2: With triethylamine In dichloromethane at 22 - 30℃; for 0.166667 - 0.25h; Stage #3: acetic anhydride With dmap In dichloromethane at 8 - 11℃; for 2.66667 - 2.75h;
With dmap; triethylamine In dichloromethane at 20℃; for 12h;

: 2-(2-((2-amino-6-chloro-5-nitrosopyrimidine-4-yl)amino)ethyl)propane-1,3-diol

: 108-24-7
acetic anhydride

: 122-51-0
orthoformic acid triethyl ester

: 104227-87-4
9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine

Conditions

Conditions	Yield
Stage #1: 2-(2-((2-amino-6-chloro-5-nitrosopyrimidine-4-yl)amino)ethyl)propane-1,3-diol With 5%-palladium/activated carbon; ammonium formate In ethyl acetate at 65℃; for 22h; Stage #2: orthoformic acid triethyl ester With acetic acid In ethyl acetate at 30℃; for 20h; Stage #3: acetic anhydride With dmap; triethylamine In ethyl acetate at 30℃; for 1.5h; Reagent/catalyst; Temperature;	92.12%

...Expand

: 225111-66-0
9-<4-acetoxy-3-(acetoxymethyl)butyl>-2-amino-6-<(4-chlorophenyl)sulfanyl>-9H-purine

: 104227-87-4
9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine

Conditions

Conditions	Yield
With nickel In ethanol; water for 1h; Heating;	91%

: 108-24-7
acetic anhydride

: 2-amino-9-(4-hydroxy-3-hydroxymethylbut-1-yl)purine hydrochloride

: 104227-87-4
9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine

Conditions

Conditions	Yield
Stage #1: 2-amino-9-(4-hydroxy-3-hydroxymethylbut-1-yl)purine hydrochloride With triethylamine In dichloromethane at 10 - 20℃; Stage #2: acetic anhydride With dmap In dichloromethane at 5 - 20℃;	91%
With dmap; triethylamine In dichloromethane at 20℃; for 2h; Acetylation;	80%
Stage #1: 2-amino-9-(4-hydroxy-3-hydroxymethylbut-1-yl)purine hydrochloride With triethylamine In dichloromethane at 10 - 20℃; for 0.25 - 0.333333h; Stage #2: acetic anhydride With dmap In dichloromethane at 5 - 20℃; for 3h;

: 104227-86-3
6-deoxypenciclovir

: 104227-87-4
9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine

Conditions

Conditions	Yield
With pyridine; dmap; acetic anhydride In tetrahydrofuran; methanol	91%

: 97845-60-8
9-<4-acetoxy-3-(acetoxymethyl)butyl>-2-amino-6-chloro-9H-purine

: 104227-87-4
9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine

Conditions

Conditions	Yield
With water; ammonium formate; palladium on charcoal In ethyl acetate for 2h; Product distribution / selectivity;	90.9%
With ammonium formate; palladium In methanol; water	90%
With ammonium formate; palladium 10% on activated carbon In methanol for 2h; Heating / reflux;	90%

: 108-24-7
acetic anhydride

: 122497-22-7
diethyl 2-(2-(2-aminopurine-9-yl)ethyl)malonate

: 104227-87-4
9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine

Conditions

Conditions	Yield
With pyridine; dmap; sodium tetrahydroborate Yield given. Multistep reaction;

: 17495-12-4
2-amino-7-benzyl-1H-purin-6(7H)-one

: 104227-87-4
9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: 93 percent / 1-methyl-pyrrolidin-2-one / 1 h / 150 °C 2: 1-methyl-pyrrolidin-2-one / 2 h / 120 °C 3: HCOONH4 / Pd/C / methanol / 4 h / Heating 4: aq. NaOH / 0.5 h / Heating 5: 83 percent / 1-methyl-pyrrolidin-2-one / 5 h / 150 °C 6: 99 percent / Et3N; DMAP / CH2Cl2 / 2.5 h / 20 °C 7: 60 percent / H2; Et3N / Pd/C / ethanol / 8 h / 80 - 85 °C / 2250.18 Torr 8: 99 percent / aq. MeNH2 / 0.25 h / 20 °C 9: 97 percent / pyridine; DMAP / tetrahydrofuran / 3 h / 20 °C View Scheme

Yield

Multi-step reaction with 9 steps
1: 93 percent / 1-methyl-pyrrolidin-2-one / 1 h / 150 °C
2: 1-methyl-pyrrolidin-2-one / 2 h / 120 °C
3: HCOONH4 / Pd/C / methanol / 4 h / Heating
4: aq. NaOH / 0.5 h / Heating
5: 83 percent / 1-methyl-pyrrolidin-2-one / 5 h / 150 °C
6: 99 percent / Et3N; DMAP / CH2Cl2 / 2.5 h / 20 °C
7: 60 percent / H2; Et3N / Pd/C / ethanol / 8 h / 80 - 85 °C / 2250.18 Torr
8: 99 percent / aq. MeNH2 / 0.25 h / 20 °C
9: 97 percent / pyridine; DMAP / tetrahydrofuran / 3 h / 20 °C
View Scheme

: 17495-10-2
N2-acetyl-7-benzylguanine

: 104227-87-4
9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 1-methyl-pyrrolidin-2-one / 2 h / 120 °C 2: HCOONH4 / Pd/C / methanol / 4 h / Heating 3: aq. NaOH / 0.5 h / Heating 4: 83 percent / 1-methyl-pyrrolidin-2-one / 5 h / 150 °C 5: 99 percent / Et3N; DMAP / CH2Cl2 / 2.5 h / 20 °C 6: 60 percent / H2; Et3N / Pd/C / ethanol / 8 h / 80 - 85 °C / 2250.18 Torr 7: 99 percent / aq. MeNH2 / 0.25 h / 20 °C 8: 97 percent / pyridine; DMAP / tetrahydrofuran / 3 h / 20 °C View Scheme

Yield

Multi-step reaction with 8 steps
1: 1-methyl-pyrrolidin-2-one / 2 h / 120 °C
2: HCOONH4 / Pd/C / methanol / 4 h / Heating
3: aq. NaOH / 0.5 h / Heating
4: 83 percent / 1-methyl-pyrrolidin-2-one / 5 h / 150 °C
5: 99 percent / Et3N; DMAP / CH2Cl2 / 2.5 h / 20 °C
6: 60 percent / H2; Et3N / Pd/C / ethanol / 8 h / 80 - 85 °C / 2250.18 Torr
7: 99 percent / aq. MeNH2 / 0.25 h / 20 °C
8: 97 percent / pyridine; DMAP / tetrahydrofuran / 3 h / 20 °C
View Scheme

: 19962-37-9
N-(6-oxo-6,9-dihydro-1H-purin-2-yl)acetamide

: 104227-87-4
9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1.1: 12.6 g / 1-methyl-pyrrolidin-2-one / 2 h / 120 °C 2.1: HCOONH4 / Pd/C / methanol / 4 h / Heating 2.2: NH4OH / 1 h / Heating 3.1: 93 percent / 1-methyl-pyrrolidin-2-one / 1 h / 150 °C 4.1: 1-methyl-pyrrolidin-2-one / 2 h / 120 °C 5.1: HCOONH4 / Pd/C / methanol / 4 h / Heating 6.1: aq. NaOH / 0.5 h / Heating 7.1: 83 percent / 1-methyl-pyrrolidin-2-one / 5 h / 150 °C 8.1: 99 percent / Et3N; DMAP / CH2Cl2 / 2.5 h / 20 °C 9.1: 60 percent / H2; Et3N / Pd/C / ethanol / 8 h / 80 - 85 °C / 2250.18 Torr 10.1: 99 percent / aq. MeNH2 / 0.25 h / 20 °C 11.1: 97 percent / pyridine; DMAP / tetrahydrofuran / 3 h / 20 °C View Scheme

Yield

Multi-step reaction with 11 steps
1.1: 12.6 g / 1-methyl-pyrrolidin-2-one / 2 h / 120 °C
2.1: HCOONH4 / Pd/C / methanol / 4 h / Heating
2.2: NH4OH / 1 h / Heating
3.1: 93 percent / 1-methyl-pyrrolidin-2-one / 1 h / 150 °C
4.1: 1-methyl-pyrrolidin-2-one / 2 h / 120 °C
5.1: HCOONH4 / Pd/C / methanol / 4 h / Heating
6.1: aq. NaOH / 0.5 h / Heating
7.1: 83 percent / 1-methyl-pyrrolidin-2-one / 5 h / 150 °C
8.1: 99 percent / Et3N; DMAP / CH2Cl2 / 2.5 h / 20 °C
9.1: 60 percent / H2; Et3N / Pd/C / ethanol / 8 h / 80 - 85 °C / 2250.18 Torr
10.1: 99 percent / aq. MeNH2 / 0.25 h / 20 °C
11.1: 97 percent / pyridine; DMAP / tetrahydrofuran / 3 h / 20 °C
View Scheme

: 73-40-5
2-amino-1,9-dihydro-6H-purin-6-one

: 104227-87-4
9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine

Conditions

Conditions	Yield
Multi-step reaction with 12 steps 1.1: 1-methyl-pyrrolidin-2-one / 4 h / 150 °C 2.1: 12.6 g / 1-methyl-pyrrolidin-2-one / 2 h / 120 °C 3.1: HCOONH4 / Pd/C / methanol / 4 h / Heating 3.2: NH4OH / 1 h / Heating 4.1: 93 percent / 1-methyl-pyrrolidin-2-one / 1 h / 150 °C 5.1: 1-methyl-pyrrolidin-2-one / 2 h / 120 °C 6.1: HCOONH4 / Pd/C / methanol / 4 h / Heating 7.1: aq. NaOH / 0.5 h / Heating 8.1: 83 percent / 1-methyl-pyrrolidin-2-one / 5 h / 150 °C 9.1: 99 percent / Et3N; DMAP / CH2Cl2 / 2.5 h / 20 °C 10.1: 60 percent / H2; Et3N / Pd/C / ethanol / 8 h / 80 - 85 °C / 2250.18 Torr 11.1: 99 percent / aq. MeNH2 / 0.25 h / 20 °C 12.1: 97 percent / pyridine; DMAP / tetrahydrofuran / 3 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: 1.) trifluoroacetic anhydride / 1) pyridine, 0 deg C, 20 min; 2) pyridine, rt, 2 h 2: potassium carbonate / dimethylformamide / 18 h / 40 °C 3: 91 percent / Raney nickel / ethanol; H2O / 1 h / Heating View Scheme
Multi-step reaction with 6 steps 1: 1.) trifluoroacetic anhydride / 1) pyridine, 0 deg C, 20 min; 2) pyridine, rt, 2 h 2: 86.6 percent / potassium carbonate / dimethylsulfoxide / 1 h / 50 °C 3: 93 percent / potassium carbonate / dimethylsulfoxide / 1.5 h / 50 °C 4: 85 percent / NaBH4 / methanol; bis-(2-methoxy-ethyl) ether / 18 h / 50 °C 5: 96 percent / pyridine / 16 h / Ambient temperature 6: 91 percent / Raney nickel / ethanol; H2O / 1 h / Heating View Scheme
Multi-step reaction with 6 steps 1: trichlorophosphate / N,N-dimethyl-formamide / 6 h / 0 °C / Reflux 2: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 12 h / 70 °C / Inert atmosphere 3: potassium carbonate / dimethyl sulfoxide / 4 h / 40 - 50 °C 4: palladium 10% on activated carbon; hydrogen; triethylamine / methanol / 7 h / 55 °C 5: methanol; sodium tetrahydroborate / dichloromethane / 2.5 h / 20 °C 6: dmap; triethylamine / dichloromethane / 12 h / 20 °C View Scheme

: 39809-25-1
Penciclovir

: 104227-87-4
9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 83 percent / 1-methyl-pyrrolidin-2-one / 5 h / 150 °C 2: 99 percent / Et3N; DMAP / CH2Cl2 / 2.5 h / 20 °C 3: 60 percent / H2; Et3N / Pd/C / ethanol / 8 h / 80 - 85 °C / 2250.18 Torr 4: 99 percent / aq. MeNH2 / 0.25 h / 20 °C 5: 97 percent / pyridine; DMAP / tetrahydrofuran / 3 h / 20 °C View Scheme

: 118-00-3
G

: 104227-87-4
9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1.1: dimethylsulfoxide / 24 h / 20 °C 1.2: 85 percent / aq. HCl / dimethylsulfoxide / 2 h / 70 °C 2.1: 93 percent / 1-methyl-pyrrolidin-2-one / 1 h / 150 °C 3.1: 1-methyl-pyrrolidin-2-one / 2 h / 120 °C 4.1: HCOONH4 / Pd/C / methanol / 4 h / Heating 5.1: aq. NaOH / 0.5 h / Heating 6.1: 83 percent / 1-methyl-pyrrolidin-2-one / 5 h / 150 °C 7.1: 99 percent / Et3N; DMAP / CH2Cl2 / 2.5 h / 20 °C 8.1: 60 percent / H2; Et3N / Pd/C / ethanol / 8 h / 80 - 85 °C / 2250.18 Torr 9.1: 99 percent / aq. MeNH2 / 0.25 h / 20 °C 10.1: 97 percent / pyridine; DMAP / tetrahydrofuran / 3 h / 20 °C View Scheme

Yield

Multi-step reaction with 10 steps
1.1: dimethylsulfoxide / 24 h / 20 °C
1.2: 85 percent / aq. HCl / dimethylsulfoxide / 2 h / 70 °C
2.1: 93 percent / 1-methyl-pyrrolidin-2-one / 1 h / 150 °C
3.1: 1-methyl-pyrrolidin-2-one / 2 h / 120 °C
4.1: HCOONH4 / Pd/C / methanol / 4 h / Heating
5.1: aq. NaOH / 0.5 h / Heating
6.1: 83 percent / 1-methyl-pyrrolidin-2-one / 5 h / 150 °C
7.1: 99 percent / Et3N; DMAP / CH2Cl2 / 2.5 h / 20 °C
8.1: 60 percent / H2; Et3N / Pd/C / ethanol / 8 h / 80 - 85 °C / 2250.18 Torr
9.1: 99 percent / aq. MeNH2 / 0.25 h / 20 °C
10.1: 97 percent / pyridine; DMAP / tetrahydrofuran / 3 h / 20 °C
View Scheme

: 97845-72-2
2-[(acetyloxy)methyl]-4-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)butyl acetate

: 104227-87-4
9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: aq. NaOH / 0.5 h / Heating 2: 83 percent / 1-methyl-pyrrolidin-2-one / 5 h / 150 °C 3: 99 percent / Et3N; DMAP / CH2Cl2 / 2.5 h / 20 °C 4: 60 percent / H2; Et3N / Pd/C / ethanol / 8 h / 80 - 85 °C / 2250.18 Torr 5: 99 percent / aq. MeNH2 / 0.25 h / 20 °C 6: 97 percent / pyridine; DMAP / tetrahydrofuran / 3 h / 20 °C View Scheme

: 256945-18-3
N2-acetyl-9-[4-acetoxy-3-(acetoxymethyl)but-1-yl]guanine

: 104227-87-4
9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 99 percent / Et3N; DMAP / CH2Cl2 / 2.5 h / 20 °C 2: 60 percent / H2; Et3N / Pd/C / ethanol / 8 h / 80 - 85 °C / 2250.18 Torr 3: 99 percent / aq. MeNH2 / 0.25 h / 20 °C 4: 97 percent / pyridine; DMAP / tetrahydrofuran / 3 h / 20 °C View Scheme

: 4-acetoxy-3-acetoxymethylbut-1-yl tosylate

: 104227-87-4
9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 1-methyl-pyrrolidin-2-one / 2 h / 120 °C 2: HCOONH4 / Pd/C / methanol / 4 h / Heating 3: aq. NaOH / 0.5 h / Heating 4: 83 percent / 1-methyl-pyrrolidin-2-one / 5 h / 150 °C 5: 99 percent / Et3N; DMAP / CH2Cl2 / 2.5 h / 20 °C 6: 60 percent / H2; Et3N / Pd/C / ethanol / 8 h / 80 - 85 °C / 2250.18 Torr 7: 99 percent / aq. MeNH2 / 0.25 h / 20 °C 8: 97 percent / pyridine; DMAP / tetrahydrofuran / 3 h / 20 °C View Scheme

Yield

: acetic acid 2-acetoxymethyl-4-(2-acetylamino-purin-9-yl)-butyl ester

: 104227-87-4
9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 99 percent / aq. MeNH2 / 0.25 h / 20 °C 2: 97 percent / pyridine; DMAP / tetrahydrofuran / 3 h / 20 °C View Scheme

: 256945-19-4
9-[4-acetoxy-3-(acetoxymethyl)but-1-yl]-2-acetylamino-6-(2',4',6'-triisopropylbenzenesulfonyloxy)-9H-purine

: 104227-87-4
9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 60 percent / H2; Et3N / Pd/C / ethanol / 8 h / 80 - 85 °C / 2250.18 Torr 2: 99 percent / aq. MeNH2 / 0.25 h / 20 °C 3: 97 percent / pyridine; DMAP / tetrahydrofuran / 3 h / 20 °C View Scheme

: N2-acetyl-7,9-dibenzylguaninium bromide

: 104227-87-4
9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1.1: HCOONH4 / Pd/C / methanol / 4 h / Heating 1.2: NH4OH / 1 h / Heating 2.1: 93 percent / 1-methyl-pyrrolidin-2-one / 1 h / 150 °C 3.1: 1-methyl-pyrrolidin-2-one / 2 h / 120 °C 4.1: HCOONH4 / Pd/C / methanol / 4 h / Heating 5.1: aq. NaOH / 0.5 h / Heating 6.1: 83 percent / 1-methyl-pyrrolidin-2-one / 5 h / 150 °C 7.1: 99 percent / Et3N; DMAP / CH2Cl2 / 2.5 h / 20 °C 8.1: 60 percent / H2; Et3N / Pd/C / ethanol / 8 h / 80 - 85 °C / 2250.18 Torr 9.1: 99 percent / aq. MeNH2 / 0.25 h / 20 °C 10.1: 97 percent / pyridine; DMAP / tetrahydrofuran / 3 h / 20 °C View Scheme

Yield

Multi-step reaction with 10 steps
1.1: HCOONH4 / Pd/C / methanol / 4 h / Heating
1.2: NH4OH / 1 h / Heating
2.1: 93 percent / 1-methyl-pyrrolidin-2-one / 1 h / 150 °C
3.1: 1-methyl-pyrrolidin-2-one / 2 h / 120 °C
4.1: HCOONH4 / Pd/C / methanol / 4 h / Heating
5.1: aq. NaOH / 0.5 h / Heating
6.1: 83 percent / 1-methyl-pyrrolidin-2-one / 5 h / 150 °C
7.1: 99 percent / Et3N; DMAP / CH2Cl2 / 2.5 h / 20 °C
8.1: 60 percent / H2; Et3N / Pd/C / ethanol / 8 h / 80 - 85 °C / 2250.18 Torr
9.1: 99 percent / aq. MeNH2 / 0.25 h / 20 °C
10.1: 97 percent / pyridine; DMAP / tetrahydrofuran / 3 h / 20 °C
View Scheme

: 9-(4-acetoxy-3-acetoxymethyl-butyl)-2-acetylamino-7-benzyl-6-oxo-6,7-dihydro-1H-purin-9-ium; bromide

: 104227-87-4
9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: HCOONH4 / Pd/C / methanol / 4 h / Heating 2: aq. NaOH / 0.5 h / Heating 3: 83 percent / 1-methyl-pyrrolidin-2-one / 5 h / 150 °C 4: 99 percent / Et3N; DMAP / CH2Cl2 / 2.5 h / 20 °C 5: 60 percent / H2; Et3N / Pd/C / ethanol / 8 h / 80 - 85 °C / 2250.18 Torr 6: 99 percent / aq. MeNH2 / 0.25 h / 20 °C 7: 97 percent / pyridine; DMAP / tetrahydrofuran / 3 h / 20 °C View Scheme

Yield

Multi-step reaction with 7 steps
1: HCOONH4 / Pd/C / methanol / 4 h / Heating
2: aq. NaOH / 0.5 h / Heating
3: 83 percent / 1-methyl-pyrrolidin-2-one / 5 h / 150 °C
4: 99 percent / Et3N; DMAP / CH2Cl2 / 2.5 h / 20 °C
5: 60 percent / H2; Et3N / Pd/C / ethanol / 8 h / 80 - 85 °C / 2250.18 Torr
6: 99 percent / aq. MeNH2 / 0.25 h / 20 °C
7: 97 percent / pyridine; DMAP / tetrahydrofuran / 3 h / 20 °C
View Scheme

: 55387-85-4
3-hydroxymethyl-4-hydroxybutanal diethyl acetal

: 104227-87-4
9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1.1: 83 percent / Dowex 50WX8-H(1+) resin / ethanol / 2 h / Heating 2.1: 99 percent / NEt3 / CH2Cl2 / 3 h / 0 - 20 °C 3.1: 47 percent / HCl / H2O; dioxane / 18 h / 20 °C 4.1: 95 percent / NEt3; DMAP; 3 Angstroem molecular sieves / acetonitrile / 1 h / 20 °C 5.1: bis(trimethylsilyl)acetamide / dimethylformamide / 1.5 h / 20 °C 5.2: 81 percent / TMSOTf / dimethylformamide / 3 h / 0 - 5 °C 6.1: 42 percent / aq. NaOH / dioxane / 4 h / 20 °C 7.1: DIBAL-H / tetrahydrofuran / 24 h / 20 °C 8.1: NEt3; DMAP / CH2Cl2 / 2 h / Heating 9.1: 81 percent / hydrogen; NEt3 / Pd/C / ethyl acetate / 4 h / 50 °C / 760 Torr View Scheme

Yield

Multi-step reaction with 9 steps
1.1: 83 percent / Dowex 50WX8-H(1+) resin / ethanol / 2 h / Heating
2.1: 99 percent / NEt3 / CH2Cl2 / 3 h / 0 - 20 °C
3.1: 47 percent / HCl / H2O; dioxane / 18 h / 20 °C
4.1: 95 percent / NEt3; DMAP; 3 Angstroem molecular sieves / acetonitrile / 1 h / 20 °C
5.1: bis(trimethylsilyl)acetamide / dimethylformamide / 1.5 h / 20 °C
5.2: 81 percent / TMSOTf / dimethylformamide / 3 h / 0 - 5 °C
6.1: 42 percent / aq. NaOH / dioxane / 4 h / 20 °C
7.1: DIBAL-H / tetrahydrofuran / 24 h / 20 °C
8.1: NEt3; DMAP / CH2Cl2 / 2 h / Heating
9.1: 81 percent / hydrogen; NEt3 / Pd/C / ethyl acetate / 4 h / 50 °C / 760 Torr
View Scheme

: 104227-87-4
9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine

: 104227-86-3
6-deoxypenciclovir

Conditions

Conditions	Yield
With ammonia In methanol for 18h; Ambient temperature;	96%

: 104227-87-4
9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine

: 98-88-4
benzoyl chloride

: C28H27N5O6

Conditions

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃; for 14h;	88%

: 4433-63-0
Ethyl boronic acid

: 104227-87-4
9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine

: 131266-23-4
9-(4-acetoxy-3-acetoxymethylbutyl)-2-amino-6-ethylpurine

Conditions

Conditions	Yield
With tris(2,2'-bipyridyl)ruthenium dichloride; 1-acetoxy-1,2-benziodoxol-3-one at 30℃; for 4h; Minisci Aromatic Substitution; Inert atmosphere; Irradiation;	70%

: 104227-87-4
9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine

: 1,3-dioxoisoindolin-2-yl cyclohexanecarboxylate

: 2-(2-(2-amino-6-cyclohexyl-9H-purin-9-yl)ethyl)propane-1,3-diyl diacetate

Conditions

Conditions	Yield
With [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; trifluoroacetic acid In N,N-dimethyl acetamide at 20℃; for 6h; Schlenk technique; Inert atmosphere; Irradiation; regioselective reaction;	54%

: 871-91-0
oct-7-yn-1-ol

: 104227-87-4
9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine

: C22H31N5O5

Conditions

Conditions	Yield
With 4,5,6,7-tetrafluoro-1-hydroxybenzo[d][1,2]iodaoxol-3(1H)-one; Ru(bpy)3Cl2 at 30℃; for 24h; Minisci Aromatic Substitution; Inert atmosphere; Irradiation; regioselective reaction;	53%

: C8H14BNO3

: 104227-87-4
9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine

: C22H30N6O5

Conditions

Conditions	Yield
With tris(2,2'-bipyridyl)ruthenium dichloride; 1-acetoxy-1,2-benziodoxol-3-one at 30℃; for 7h; Minisci Aromatic Substitution; Inert atmosphere; Irradiation;	51%

: 4441-56-9
cyclohexylboronic acid

: 104227-87-4
9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine

: 2-(2-(2-amino-6-cyclohexyl-9H-purin-9-yl)ethyl)propane-1,3-diyl diacetate

Conditions

Conditions	Yield
With tris(2,2'-bipyridyl)ruthenium dichloride; 1-acetoxy-1,2-benziodoxol-3-one at 30℃; for 4h; Minisci Aromatic Substitution; Inert atmosphere; Irradiation;	50%

: 3721-95-7
Cyclobutanecarboxylic acid

: 104227-87-4
9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine

: C18H25N5O4

Conditions

Conditions	Yield
With copper(I) thiophene-2-carboxylate; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(5-methyl-2-(4-fluorophenyl)pyridine(-1H))-iridium(III) hexafluorophosphate; N,N,N′,N′-tetramethyl-N″-tert-butylguanidine; bathophenanthroline; iodomesitylene diacetate In 1,4-dioxane at 20℃; for 1h; Inert atmosphere; Irradiation; regioselective reaction;	40%

: 104227-87-4
9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine

: 120687-07-2
(R,S)-9-<4-acetoxy-3-(hydroxymethyl)but-1-yl>-2-aminopurine

Conditions

Conditions	Yield
With potassium carbonate In methanol for 0.333333h;	30%
With esterase from Escherichia coli host strain; oxygen In dimethyl sulfoxide at 30℃; pH=7.4; Enzymatic reaction;

: 104227-87-4
9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine

A 9-(4-acetoxy-3-hydroxymethyl-1-yl)-2-aminopurine: 9-(4-acetoxy-3-hydroxymethyl-1-yl)-2-aminopurine

B: 120687-07-2
(R,S)-9-<4-acetoxy-3-(hydroxymethyl)but-1-yl>-2-aminopurine

Conditions

Conditions	Yield
With potassium carbonate In methanol; acetic acid	A n/a B 30%

: 104227-87-4
9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine

: 39809-25-1
Penciclovir

Conditions

Conditions	Yield
With oxygen In water for 2.5h; cows' milk xanthine oxidase, pH 7; Yield given;

Famciclovir Specification

1. Introduction of Famciclovir

Famciclovir, with the IUPAC Name of [2-(acetyloxymethyl)-4-(2-aminopurin-9-yl)butyl] acetate, is one kind of Off-White Powder. And this chemical belongs to the Product Categories which include Intermediates; Intermediates & Fine Chemicals; Pharmaceuticals; API's.

2. Properties of Famciclovir

Famciclovir has the following datas: (1)Melting Point: 102-104°C; (2)Boiling point: 550.2 °C at 760 mmHg; (3)Flash Point: 286.6 °C; (4)Density: 1.4 g/cm³; (5)Index of Refraction: 1.628; (6)Molar Refractivity: 81.11 cm³; (7)Molar Volume: 228.4 cm³; (8)Surface Tension: 54.3 dyne/cm; (9)Enthalpy of Vaporization: 83.02 kJ/mol; (10)Vapour Pressure: 3.73E-12 mmHg at 25°C.

3. Structure Descriptors of Famciclovir

(1). Canonical SMILES: CC(=O)OCC(CCN1C=NC2=CN=C(N=C21)N)COC(=O)C
(2). InChI: InChI=1S/C14H19N5O4/c1-9(20)22-6-11(7-23-10(2)21)3-4-19-8-17-12-5-16-14(15)18-13(12)19/h5,8,11H,3-4,6-7H2,1-2H3,(H2,15,16,18)
(3). InChIKey: GGXKWVWZWMLJEH-UHFFFAOYSA-N

4. Use of Famciclovir

Famciclovir is a guanine analogue antiviral drug and it's used for the treatment of various herpesvirus infections, especial for herpes zoster (shingles). Famciclovir comes as a tablet to take by mouth. It is usually taken every three times a day for 7 days to treat shingles. If it's used to treat genital herpes, famciclovir is usually taken twice a day for 5 days. It is also sometimes given in one single large dose as opposed to several days of scheduled small doses. Take famciclovir with food or milk.

5. Safety information of Famciclovir

Safety Information of Famciclovir (CAS NO.104227-87-4):
Hazard Codes: T Toxic
Risk Statements: 20/21/22-45-61
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
R45:May cause cancer.
R61:May cause harm to the unborn child.
Safety Statements: 36/37/39-45-53
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.)
S53:Avoid exposure - obtain special instructions before use.

Product Name

Famciclovir

Synthetic route

Famciclovir Specification

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