[3-[(2-amino-6-oxo-3H-purin-9-yl)methoxy]-4-hydroxy-butyl]phosphonic a cid

Base Information

• Chemical Name: [3-[(2-amino-6-oxo-3H-purin-9-yl)methoxy]-4-hydroxy-butyl]phosphonic a cid
• CAS No.: 104880-60-6
• Molecular Formula: C₁₀H₁₆N₅O₆P
• Molecular Weight: 333.241
• Mol file: 104880-60-6.mol

Synonyms:Phosphonicacid, [3-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]-4-hydroxybutyl]-(9CI); SR 3745A

Chemical Property of [3-[(2-amino-6-oxo-3H-purin-9-yl)methoxy]-4-hydroxy-butyl]phosphonic a cid

Chemical Property:

• Vapor Pressure: 1.27E-26mmHg at 25°C
• Boiling Point: 794.6°Cat760mmHg
• Flash Point: 434.4°C
• PSA: 186.39000
• Density: 1.94g/cm³
• LogP: -0.81420

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of [3-[(2-amino-6-oxo-3H-purin-9-yl)methoxy]-4-hydroxy-butyl]phosphonic a cid

There total 4 articles about [3-[(2-amino-6-oxo-3H-purin-9-yl)methoxy]-4-hydroxy-butyl]phosphonic a cid 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: 88.0%

9-<<1--4-hydroxy-3-butoxy>-methyl>guanine (100683-71-4) → 3-((2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)-4-hydroxybutylphosphonic acid (104880-60-6)

Guidance literature:

With hydrogen; palladium dihydroxide; In ethanol; water; cyclohexene; for 4h; Heating;

DOI:10.1021/jm00155a015

Reference yield:

ganciclovir (82410-32-0) → 3-((2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)-4-hydroxybutylphosphonic acid (104880-60-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 43 percent / triethylamine, 4-(dimethylamino)pyridine / dimethylformamide / 2 h / 40 °C

2: 9.5 g / dicyclohexylcarbodiimide, methylphosphonic acid / dimethylsulfoxide / 1.) 18 deg C, 5 h, 2.) RT, 16 h

3: 43 percent / triethylamine / tetrahydrofuran / 168 h / Ambient temperature

4: 88 percent / potassium azodicarboxylate, pyridine / acetic acid / 144 h / Ambient temperature

5: 78 percent / NaH / dimethylsulfoxide / 0.05 h

6: 65 percent / 80percent aq. acetic acid / 2 h / 80 °C

7: 88 percent / H₂ / 20percent Pd(OH)2/C / cyclohexene; ethanol; H₂O / 4 h / Heating

With pyridine; dmap; methylphosphonic acid; hydrogen; potassium diazodicarboxylate; sodium hydride; acetic acid; triethylamine; dicyclohexyl-carbodiimide; palladium dihydroxide; In tetrahydrofuran; ethanol; water; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide; cyclohexene;

DOI:10.1021/jm00155a015

Reference yield:

3-[(4-Methoxy-phenyl)-diphenyl-methoxy]-2-(2-{[(4-methoxy-phenyl)-diphenyl-methyl]-amino}-6-oxo-1,6-dihydro-purin-9-ylmethoxy)-propionaldehyde (100683-69-0) → 3-((2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)-4-hydroxybutylphosphonic acid (104880-60-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 43 percent / triethylamine / tetrahydrofuran / 168 h / Ambient temperature

2: 88 percent / potassium azodicarboxylate, pyridine / acetic acid / 144 h / Ambient temperature

3: 78 percent / NaH / dimethylsulfoxide / 0.05 h

4: 65 percent / 80percent aq. acetic acid / 2 h / 80 °C

5: 88 percent / H₂ / 20percent Pd(OH)2/C / cyclohexene; ethanol; H₂O / 4 h / Heating

With pyridine; hydrogen; potassium diazodicarboxylate; sodium hydride; acetic acid; triethylamine; palladium dihydroxide; In tetrahydrofuran; ethanol; water; acetic acid; dimethyl sulfoxide; cyclohexene;

DOI:10.1021/jm00155a015

upstream raw materials:

9-<<1--4-hydroxy-3-butoxy>-methyl>guanine

ganciclovir

3-[(4-Methoxy-phenyl)-diphenyl-methoxy]-2-(2-{[(4-methoxy-phenyl)-diphenyl-methyl]-amino}-6-oxo-1,6-dihydro-purin-9-ylmethoxy)-propionaldehyde

9-[({1-hydroxy-3-[(4-methoxyphenyl)-diphenylmethoxy]propan-2-yl}oxy)methyl]-2-{[(4-methoxyphenyl)diphenylmethyl]amino}-6,9-dihydro-1H-purin-6-one

Refernces