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

Base Information

Chemical Name:5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-2'-deoxy-3'-O-diethylphosphorylthymidine
CAS No.:470699-98-0
Molecular Formula:C₃₂H₄₀BrN₂O₉PS
Molecular Weight:739.621
Hs Code.:

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

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

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

There total 7 articles about 5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-2'-deoxy-3'-O-diethylphosphorylthymidine 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-3-(diethoxy-phosphanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-carbothioic acid S-[2-(2-bromo-phenyl)-2-methyl-propyl] ester

: 470699-98-0
5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-2'-deoxy-3'-O-diethylphosphorylthymidine

Guidance literature:: With 2,6-dimethylpyridine; iodine; In tetrahydrofuran; dichloromethane; water;
DOI:10.1016/S0040-4020(02)00557-4

Reference yield:

: 177748-64-0
2-(2-bromophenyl)-2-methylpropan-1-ol

: 470699-98-0
5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-2'-deoxy-3'-O-diethylphosphorylthymidine

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: 76 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

Reference yield:

: 208175-42-2
5'-O-benzyl-3'-O-(tert-butyldimethylsilyl)-2'-deoxy-4'α-methoxycarbonyl-D-thymidine

: 470699-98-0
5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-2'-deoxy-3'-O-diethylphosphorylthymidine

Guidance literature:: Multi-step reaction with 4 steps

1: 93 percent / potassium tert-butoxide / tetrahydrofuran; H₂O

2: 76 percent / BOP-Cl; triethylamine / tetrahydrofuran; CH₂Cl₂ / 2 h / Heating

3: DMAP / CH₂Cl₂ / 0 °C

4: 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