5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-6-N-(tert-butyloxycarbonyl)-2'-deoxy-3'-O-diethylphosphoryladenosine

Base Information

• Chemical Name: 5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-6-N-(tert-butyloxycarbonyl)-2'-deoxy-3'-O-diethylphosphoryladenosine
• CAS No.: 470699-91-3
• Molecular Formula: C₃₇H₄₇BrN₅O₉PS
• Molecular Weight: 848.752
• Mol file: 470699-91-3.mol

Synonyms:5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-6-N-(tert-butyloxycarbonyl)-2'-deoxy-3'-O-diethylphosphoryladenosine

Chemical Property of 5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-6-N-(tert-butyloxycarbonyl)-2'-deoxy-3'-O-diethylphosphoryladenosine

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]-6-N-(tert-butyloxycarbonyl)-2'-deoxy-3'-O-diethylphosphoryladenosine

There total 9 articles about 5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-6-N-(tert-butyloxycarbonyl)-2'-deoxy-3'-O-diethylphosphoryladenosine 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:

2-benzyloxymethyl-5-(6-tert-butoxycarbonylamino-purin-9-yl)-3-(diethoxy-phosphanyloxy)-tetrahydro-furan-2-carbothioic acid S-[2-(2-bromo-phenyl)-2-methyl-propyl] ester → 5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-6-N-(tert-butyloxycarbonyl)-2'-deoxy-3'-O-diethylphosphoryladenosine (470699-91-3)

Guidance literature:

With 2,6-dimethylpyridine; iodine; In tetrahydrofuran; dichloromethane; water;

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]-6-N-(tert-butyloxycarbonyl)-2'-deoxy-3'-O-diethylphosphoryladenosine (470699-91-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / triethylamine; DMAP / CH₂Cl₂ / 1 h / 20 °C

2: 66 percent / potassium tert-butoxide / tetrahydrofuran; H₂O

3: 73 percent / BOP-Cl; triethylamine / tetrahydrofuran; CH₂Cl₂ / 2 h / Heating

4: DMAP / CH₂Cl₂ / 0 °C

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

With 2,6-dimethylpyridine; dmap; potassium tert-butylate; iodine; 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]-6-N-(tert-butyloxycarbonyl)-2'-deoxy-3'-O-diethylphosphoryladenosine (470699-91-3)

Guidance literature:

Multi-step reaction with 5 steps

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

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

3: 73 percent / BOP-Cl; triethylamine / tetrahydrofuran; CH₂Cl₂ / 2 h / Heating

4: DMAP / CH₂Cl₂ / 0 °C

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

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

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

upstream raw materials:

di-tert-butyl dicarbonate

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

5'-O-benzyl-6-N-benzoyl-3'-O-(tert-butyldimethylsilyl)-2'-deoxy-4'α-methoxycarbonyl-D-adenosine

2-(2-bromophenyl)-2-methylpropanethiol

Downstream raw materials:

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