9-(3-hydroxy-2-phosphonomethoxypropyl)guanine

Base Information

• Chemical Name: 9-(3-hydroxy-2-phosphonomethoxypropyl)guanine
• CAS No.: 113852-36-1
• Molecular Formula: C₉H₁₄N₅O₆P
• Molecular Weight: 319.214
• Mol file: 113852-36-1.mol

Synonyms:Phosphonicacid, [[2-(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)-1-(hydroxymethyl)ethoxy]methyl]-(9CI); Phosphonic acid,[[2-(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)-1-(hydroxymethyl)ethoxy]methyl]-,(?à)-

Chemical Property of 9-(3-hydroxy-2-phosphonomethoxypropyl)guanine

Chemical Property:

• Vapor Pressure: 7.81E-28mmHg at 25°C
• Boiling Point: 811.6°Cat760mmHg
• Flash Point: 444.6°C
• PSA: 186.39000
• Density: 2.05g/cm³
• LogP: -1.20430

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 9-(3-hydroxy-2-phosphonomethoxypropyl)guanine

There total 5 articles about 9-(3-hydroxy-2-phosphonomethoxypropyl)guanine 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:

(R)-6-O-benzyl-9-<3-(benzyloxy)-2-<(diisopropylphosphono)methoxy>propyl>guanine (151223-24-4) → 9-(S)-(3-hydroxy-2-phosphonomethoxypropyl)guanine (113852-36-1,117086-98-3,138332-09-9,116558-95-3)

Guidance literature:

Multi-step reaction with 2 steps

1: cyclohexene / 20percent Pd(OH)2/C / ethanol / 72 h / Heating

2: bromotrimethylsilane / acetonitrile / 14 h / Ambient temperature

With trimethylsilyl bromide; cyclohexene; palladium dihydroxide; In ethanol; acetonitrile;

DOI:10.1021/jm00094a005

Reference yield:

2-Amino-6-benzyloxypurine (19916-73-5) → 9-(S)-(3-hydroxy-2-phosphonomethoxypropyl)guanine (113852-36-1,117086-98-3,138332-09-9,116558-95-3)

Guidance literature:

Multi-step reaction with 3 steps

1: cesium carbonate / acetonitrile / 16 h / Heating

2: cyclohexene / 20percent Pd(OH)2/C / ethanol / 72 h / Heating

3: bromotrimethylsilane / acetonitrile / 14 h / Ambient temperature

With trimethylsilyl bromide; caesium carbonate; cyclohexene; palladium dihydroxide; In ethanol; acetonitrile;

DOI:10.1021/jm00094a005

Reference yield:

(R)-9-<2-<(diisopropylphosphono)methoxy>-3-hydroxypropyl>guanine (138247-69-5,148873-58-9) → 9-(S)-(3-hydroxy-2-phosphonomethoxypropyl)guanine (113852-36-1,117086-98-3,138332-09-9,116558-95-3)

Guidance literature:

With trimethylsilyl bromide; water; Yield given. Multistep reaction; 1.) CH₃CN, RT, overnight, 2.) 30 min;

DOI:10.1135/cccc19930649

upstream raw materials:

(R)-9-<2-<(diisopropylphosphono)methoxy>-3-hydroxypropyl>guanine

(R)-6-O-benzyl-9-<3-(benzyloxy)-2-<(diisopropylphosphono)methoxy>propyl>guanine

2-Amino-6-benzyloxypurine

Refernces

• 1、 Yu,Bronson,Yang,Patick,Alam,Brankovan,Datema,Hitchcock,Martin. "Synthesis and antiviral activity of methyl derivatives of 9-[2- (phosphonomethoxy)ethyl]guanine". . p. 2958 - 2969. Retrieved 2007/10/02.