4-(2-amino-6-oxo-3,6-dihydro-9H-purin-9-yl)-2-[(hexanoyloxy)methyl]butyl hexanoate

Base Information

• Chemical Name: 4-(2-amino-6-oxo-3,6-dihydro-9H-purin-9-yl)-2-[(hexanoyloxy)methyl]butyl hexanoate
• CAS No.: 97845-74-4
• Molecular Formula: C22H35N5O5
• Molecular Weight: 449.55
• Mol file: 97845-74-4.mol

Synonyms:

Chemical Property of 4-(2-amino-6-oxo-3,6-dihydro-9H-purin-9-yl)-2-[(hexanoyloxy)methyl]butyl hexanoate

Chemical Property:

• Vapor Pressure: 1.31E-16mmHg at 25°C
• Boiling Point: 646.7°C at 760 mmHg
• Flash Point: 344.9°C
• Density: 1.26g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-(2-amino-6-oxo-3,6-dihydro-9H-purin-9-yl)-2-[(hexanoyloxy)methyl]butyl hexanoate

There total 6 articles about 4-(2-amino-6-oxo-3,6-dihydro-9H-purin-9-yl)-2-[(hexanoyloxy)methyl]butyl hexanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 45.0%

Penciclovir (39809-25-1) + hexanoic acid (142-62-1) → 9-<4-(hexanoyloxy)-3-<(hexanoyloxy)methyl>but-1-yl>guanine (97845-74-4)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; for 64h; Ambient temperature;

DOI:10.1021/jm00392a020

Reference yield:

2-(hydroxymethyl)butane-1,4-diol (6482-32-2) → 9-<4-(hexanoyloxy)-3-<(hexanoyloxy)methyl>but-1-yl>guanine (97845-74-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 41 percent / p-TsOH*H₂O / tetrahydrofuran / 0.5 h / Ambient temperature

2: 87 percent / CBr₄, PPh₃ / dimethylformamide / 0.5 h / 0 °C

3: 64 percent / K₂CO₃ / dimethylformamide / 5 h / Ambient temperature

4: 72 percent / 2.0 M HCl / 1.25 h / Heating

5: 45 percent / dicyclohexylcarbodiimide, 4-(dimethylamino)pyridine / dimethylformamide / 64 h / Ambient temperature

With hydrogenchloride; dmap; carbon tetrabromide; potassium carbonate; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; triphenylphosphine; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jm00392a020

Reference yield:

triethyl 1,1,2-ethanetricarboxylate (7459-46-3) → 9-<4-(hexanoyloxy)-3-<(hexanoyloxy)methyl>but-1-yl>guanine (97845-74-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 100 percent / sodium borohydride, MeOH / 2-methyl-propan-2-ol / 0.5 h / Heating

2: 41 percent / p-TsOH*H₂O / tetrahydrofuran / 0.5 h / Ambient temperature

3: 87 percent / CBr₄, PPh₃ / dimethylformamide / 0.5 h / 0 °C

4: 64 percent / K₂CO₃ / dimethylformamide / 5 h / Ambient temperature

5: 72 percent / 2.0 M HCl / 1.25 h / Heating

6: 45 percent / dicyclohexylcarbodiimide, 4-(dimethylamino)pyridine / dimethylformamide / 64 h / Ambient temperature

With hydrogenchloride; methanol; dmap; sodium tetrahydroborate; carbon tetrabromide; potassium carbonate; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; triphenylphosphine; In tetrahydrofuran; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1021/jm00392a020

upstream raw materials:

Penciclovir

hexanoic acid

triethyl 1,1,2-ethanetricarboxylate

2-(hydroxymethyl)butane-1,4-diol

Refernces