5'-Guanylic acid, N-(4-butylphenyl)-2'-deoxy-

Base Information

• Chemical Name: 5'-Guanylic acid, N-(4-butylphenyl)-2'-deoxy-
• CAS No.: 87782-03-4
• Molecular Formula: C₂₀H₂₆N₅O₇P
• Molecular Weight: 479.429
• Mol file: 87782-03-4.mol

Synonyms:

Chemical Property of 5'-Guanylic acid, N-(4-butylphenyl)-2'-deoxy-

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5'-Guanylic acid, N-(4-butylphenyl)-2'-deoxy-

There total 10 articles about 5'-Guanylic acid, N-(4-butylphenyl)-2'-deoxy- 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:

(4-Butyl-phenyl)-trimethylsilanyl-(9-trimethylsilanyl-6-trimethylsilanyloxy-9H-purin-2-yl)-amine → N2-(p-n-butylphenyl)-2'-deoxyguanosine 5'-phosphate (87782-03-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) trimethylsilyl trifluoromethanesulfonate, 2.) NaOCH₃ / 1.) 1,2-dichloroethane, benzene, RT, 2 h, 2.) 60 deg C, 1 h

2: 1.) POCl₃, trimethyl phosphate, 2.) Et₃N / 1.) 0 deg C - 5 deg C

With trimethyl phosphite; trimethylsilyl trifluoromethanesulfonate; sodium methylate; triethylamine; trichlorophosphate;

DOI:10.1021/jm00368a012

Reference yield:

2-bromo-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)hypoxanthine (41623-91-0) → N2-(p-n-butylphenyl)-2'-deoxyguanosine 5'-phosphate (87782-03-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 56 percent / 2-methoxy-ethanol / 1.5 h / Heating

2: 98 percent / aq. NH₃ / ethanol / 72 h

3: 81 percent / pyridine / Ambient temperature

4: 83 percent / dimethylformamide / 4.5 h / 35 °C

5: 92 percent / tri-n-butyltin hydride, 2,2'-azobis<2-methylpropionitrile> / toluene / 2 h / Heating

6: 87.4 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h

7: 1.) POCl₃, trimethyl phosphate, 2.) Et₃N / 1.) 0 deg C - 5 deg C

With pyridine; trimethyl phosphite; ammonium hydroxide; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; triethylamine; trichlorophosphate; In tetrahydrofuran; ethanol; 2-methoxy-ethanol; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm00368a012

Reference yield:

2-Bromo-9-trimethylsilanyl-6-trimethylsilanyloxy-9H-purine → N2-(p-n-butylphenyl)-2'-deoxyguanosine 5'-phosphate (87782-03-4)

Guidance literature:

Multi-step reaction with 8 steps

1: trimethylsilyl trifluoromethanesulfonate / acetonitrile / 0.25 h / Heating

2: 56 percent / 2-methoxy-ethanol / 1.5 h / Heating

3: 98 percent / aq. NH₃ / ethanol / 72 h

4: 81 percent / pyridine / Ambient temperature

5: 83 percent / dimethylformamide / 4.5 h / 35 °C

6: 92 percent / tri-n-butyltin hydride, 2,2'-azobis<2-methylpropionitrile> / toluene / 2 h / Heating

7: 87.4 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h

8: 1.) POCl₃, trimethyl phosphate, 2.) Et₃N / 1.) 0 deg C - 5 deg C

With pyridine; trimethyl phosphite; ammonium hydroxide; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; triethylamine; trichlorophosphate; In tetrahydrofuran; ethanol; 2-methoxy-ethanol; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/jm00368a012

upstream raw materials:

N2-(p-n-Butylphenyl)-9-(2-deoxy-β-D-ribofuranosyl)guanine

2-bromo-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)hypoxanthine

N²-(p-n-butylphenyl)-9-<2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisilox-1,3-diyl)-β-D-ribofuranosyl>guanine

N²-(4-n-butylphenyl)-2',3',5'-O-triacetylguanosine

Downstream raw materials:

C₂₀H₂₇N₅O₁₀P₂

N²-(p-n-butylphenyl)-2'-deoxyguanosine 5'-triphosphate

Refernces