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

Base Information

• Chemical Name: 5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-4-N-(tert-butyloxycarbonyl)-2'-deoxycytidine
• CAS No.: 470699-83-3
• Molecular Formula: C₃₂H₃₈BrN₃O₇S
• Molecular Weight: 688.64
• Mol file: 470699-83-3.mol

Synonyms:5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-4-N-(tert-butyloxycarbonyl)-2'-deoxycytidine

Chemical Property of 5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-4-N-(tert-butyloxycarbonyl)-2'-deoxycytidine

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]-4-N-(tert-butyloxycarbonyl)-2'-deoxycytidine

There total 6 articles about 5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-4-N-(tert-butyloxycarbonyl)-2'-deoxycytidine 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: 67.0%

2-(2-bromophenyl)-2-methylpropanethiol (470699-76-4) + 5'-O-benzyl-4-N-(tert-butyloxycarbonyl)-4'α-carboxyl-2'-deoxycytidine (470699-81-1) → 5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-4-N-(tert-butyloxycarbonyl)-2'-deoxycytidine (470699-83-3)

Guidance literature:

With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; In tetrahydrofuran; dichloromethane; for 2h; Heating;

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

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → 5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-4-N-(tert-butyloxycarbonyl)-2'-deoxycytidine (470699-83-3)

Guidance literature:

Multi-step reaction with 3 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

With dmap; potassium tert-butylate; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; In tetrahydrofuran; dichloromethane; water;

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]-4-N-(tert-butyloxycarbonyl)-2'-deoxycytidine (470699-83-3)

Guidance literature:

Multi-step reaction with 3 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

With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; diisobutylaluminium hydride; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 1: Mitsunobu reaction;

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

upstream raw materials:

2-(2-bromophenyl)-2-methylpropanethiol

5'-O-benzyl-4-N-(tert-butyloxycarbonyl)-4'α-carboxyl-2'-deoxycytidine

di-tert-butyl dicarbonate

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

Downstream raw materials:

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

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