Phenyl-phosphonothioic acid O-[(2S,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-2,5-dihydro-furan-2-ylmethyl] ester; compound with ammonia

Base Information

• Chemical Name: Phenyl-phosphonothioic acid O-[(2S,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-2,5-dihydro-furan-2-ylmethyl] ester; compound with ammonia
• CAS No.: 142068-06-2
• Molecular Formula: C₁₅H₁₆N₃O₄PS*H₃N
• Molecular Weight: 382.38
• Mol file: 142068-06-2.mol

Synonyms:

Chemical Property of Phenyl-phosphonothioic acid O-[(2S,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-2,5-dihydro-furan-2-ylmethyl] ester; compound with ammonia

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Phenyl-phosphonothioic acid O-[(2S,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-2,5-dihydro-furan-2-ylmethyl] ester; compound with ammonia

There total 8 articles about Phenyl-phosphonothioic acid O-[(2S,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-2,5-dihydro-furan-2-ylmethyl] ester; compound with ammonia 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:

N4-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-didehydro-2',3'-dideoxycytidine (142068-16-4) → Phenyl-phosphonothioic acid O-[(2S,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-2,5-dihydro-furan-2-ylmethyl] ester; compound with ammonia (142068-06-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature

2: 1.) N-methylimidazole, 2.) H₂O, Et₃N / 1.) THF, 45 min, 2.) 10 min

3: 30percent aq. NH₄OH / Ambient temperature

With 1-methyl-1H-imidazole; ammonium hydroxide; tetrabutyl ammonium fluoride; water; triethylamine; In tetrahydrofuran;

DOI:10.1021/jm00093a003

Reference yield:

Dithiocarbonic acid O-[(2R,3R,4R,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-dithiocarboxyoxy-tetrahydro-furan-3-yl] ester → Phenyl-phosphonothioic acid O-[(2S,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-2,5-dihydro-furan-2-ylmethyl] ester; compound with ammonia (142068-06-2)

Guidance literature:

Multi-step reaction with 5 steps

1: tetrahydrofuran / 0.5 h

2: 65 percent / tri-n-butyltin hydride, azobisisobutyronitrile / toluene / 1 h / Heating

3: 88 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature

4: 1.) N-methylimidazole, 2.) H₂O, Et₃N / 1.) THF, 45 min, 2.) 10 min

5: 30percent aq. NH₄OH / Ambient temperature

With 1-methyl-1H-imidazole; ammonium hydroxide; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; water; tri-n-butyl-tin hydride; triethylamine; In tetrahydrofuran; toluene;

DOI:10.1021/jm00093a003

Reference yield:

N4-5'-O-(tert-butyldimethylsilyl)-2',3'-bis-O-<(methylthio)thiocarbonyl>cytidine (142102-28-1) → Phenyl-phosphonothioic acid O-[(2S,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-2,5-dihydro-furan-2-ylmethyl] ester; compound with ammonia (142068-06-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 65 percent / tri-n-butyltin hydride, azobisisobutyronitrile / toluene / 1 h / Heating

2: 88 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature

3: 1.) N-methylimidazole, 2.) H₂O, Et₃N / 1.) THF, 45 min, 2.) 10 min

4: 30percent aq. NH₄OH / Ambient temperature

With 1-methyl-1H-imidazole; ammonium hydroxide; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; water; tri-n-butyl-tin hydride; triethylamine; In tetrahydrofuran; toluene;

DOI:10.1021/jm00093a003

upstream raw materials:

N⁴-benzoyl-2',3'-didehydro-2',3'-dideoxycytidine

N⁴-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-didehydro-2',3'-dideoxycytidine

N⁴-5'-O-(tert-butyldimethylsilyl)-2',3'-bis-O-<(methylthio)thiocarbonyl>cytidine

N⁴-benzoyl-5'-O-(tert-butyldimethylsilyl)cytidine