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

Base Information

Chemical Name:5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-6-N-(tert-butyloxycarbonyl)-2'-deoxyadenosine
CAS No.:470699-89-9
Molecular Formula:C₃₃H₃₈BrN₅O₆S
Molecular Weight:712.665
Hs Code.:

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

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

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Technology Process of 5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-6-N-(tert-butyloxycarbonyl)-2'-deoxyadenosine

There total 6 articles about 5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-6-N-(tert-butyloxycarbonyl)-2'-deoxyadenosine 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: 73.0%

: 470699-76-4
2-(2-bromophenyl)-2-methylpropanethiol

: 470699-87-7
5'-O-benzyl-6-N-(tert-butyloxycarbonyl)-4'α-carboxyl-2'-deoxyadenosine

: 470699-89-9
5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-6-N-(tert-butyloxycarbonyl)-2'-deoxyadenosine

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:

: 24424-99-5
di-tert-butyl dicarbonate

: 470699-89-9
5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-6-N-(tert-butyloxycarbonyl)-2'-deoxyadenosine

Guidance literature:: Multi-step reaction with 3 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

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:

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

: 470699-89-9
5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-6-N-(tert-butyloxycarbonyl)-2'-deoxyadenosine

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: 73 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