5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-2'-deoxy-3'-O-diethylphosphorylcytidine

Base Information

• Chemical Name: 5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-2'-deoxy-3'-O-diethylphosphorylcytidine
• CAS No.: 470700-00-6
• Molecular Formula: C₃₁H₃₉BrN₃O₈PS
• Molecular Weight: 724.61
• Mol file: 470700-00-6.mol

Synonyms:5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-2'-deoxy-3'-O-diethylphosphorylcytidine

Chemical Property of 5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-2'-deoxy-3'-O-diethylphosphorylcytidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-2'-deoxy-3'-O-diethylphosphorylcytidine

There total 9 articles about 5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-2'-deoxy-3'-O-diethylphosphorylcytidine 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: 91.0%

5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-4-N-(tert-butyloxycarbonyl)-2'-deoxy-3'-O-diethylphosphorylcytidine (470699-85-5) → 5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-2'-deoxy-3'-O-diethylphosphorylcytidine (470700-00-6)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1016/S0040-4020(02)00557-4

Reference yield:

2-(2-bromophenyl)-2-methylpropan-1-ol (177748-64-0) → 5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-2'-deoxy-3'-O-diethylphosphorylcytidine (470700-00-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 77 percent / PPh₃; DEAD / tetrahydrofuran / 18 h

2: 96 percent / DIBALH / diethyl ether; toluene / 0.5 h / -78 - 0 °C

3: 67 percent / BOP-Cl; triethylamine / tetrahydrofuran; CH₂Cl₂ / 2 h / Heating

4: DMAP / CH₂Cl₂ / 0 °C

5: iodine; 2,6-lutidine / CH₂Cl₂; tetrahydrofuran; H₂O

6: 91 percent / trifluoroacetic acid / CH₂Cl₂ / 2 h / 20 °C

With 2,6-dimethylpyridine; dmap; iodine; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; diisobutylaluminium hydride; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; dichloromethane; water; toluene; 1: Mitsunobu reaction;

DOI:10.1016/S0040-4020(02)00557-4

Reference yield:

5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-2-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-carboxylic acid methyl ester (470699-74-2) → 5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-2'-deoxy-3'-O-diethylphosphorylcytidine (470700-00-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 77 percent / triethylamine; DMAP / CH₂Cl₂ / 5 h / 20 °C

2: 98 percent / potassium tert-butoxide / tetrahydrofuran; H₂O

3: 67 percent / BOP-Cl; triethylamine / tetrahydrofuran; CH₂Cl₂ / 2 h / Heating

4: DMAP / CH₂Cl₂ / 0 °C

5: iodine; 2,6-lutidine / CH₂Cl₂; tetrahydrofuran; H₂O

6: 91 percent / trifluoroacetic acid / CH₂Cl₂ / 2 h / 20 °C

With 2,6-dimethylpyridine; dmap; potassium tert-butylate; iodine; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/S0040-4020(02)00557-4

upstream raw materials:

5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-4-N-(tert-butyloxycarbonyl)-2'-deoxy-3'-O-diethylphosphorylcytidine

2-(2-bromophenyl)-2-methylpropan-1-ol

5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-2-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-carboxylic acid methyl ester

2-(2-bromophenyl)-2-methylpropanethiol

Downstream raw materials:

Diethyl phosphate

2,3-dihydro-3,3-dimethylbenzo[b]thiophene