5'-O-benzyl-2'-deoxy-3'-O-diethylphosphoryl-4'α-{[(2-(2-iodophenyl)ethyl)thio]carbonyl}adenosine

Base Information

Chemical Name:5'-O-benzyl-2'-deoxy-3'-O-diethylphosphoryl-4'α-{[(2-(2-iodophenyl)ethyl)thio]carbonyl}adenosine
CAS No.:470700-01-7
Molecular Formula:C₃₀H₃₅IN₅O₇PS
Molecular Weight:767.581
Hs Code.:

Synonyms:5'-O-benzyl-2'-deoxy-3'-O-diethylphosphoryl-4'α-{[(2-(2-iodophenyl)ethyl)thio]carbonyl}adenosine

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Chemical Property of 5'-O-benzyl-2'-deoxy-3'-O-diethylphosphoryl-4'α-{[(2-(2-iodophenyl)ethyl)thio]carbonyl}adenosine

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Technology Process of 5'-O-benzyl-2'-deoxy-3'-O-diethylphosphoryl-4'α-{[(2-(2-iodophenyl)ethyl)thio]carbonyl}adenosine

There total 6 articles about 5'-O-benzyl-2'-deoxy-3'-O-diethylphosphoryl-4'α-{[(2-(2-iodophenyl)ethyl)thio]carbonyl}adenosine 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: 88.0%

: 470699-90-2
5'-O-benzyl-6-N-(tert-butyloxycarbonyl)-2'-deoxy-3'-O-diethylphosphoryl-4'α-{[(2-(2-iodophenyl)ethyl)thio]carbonyl}adenosine

: 470700-01-7
5'-O-benzyl-2'-deoxy-3'-O-diethylphosphoryl-4'α-{[(2-(2-iodophenyl)ethyl)thio]carbonyl}adenosine

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 0.833333h;
DOI:10.1016/S0040-4020(02)00557-4

Reference yield:

: 208175-48-8
5'-O-benzyl-6-N-benzoyl-3'-O-(tert-butyldimethylsilyl)-2'-deoxy-4'α-methoxycarbonyl-D-adenosine

: 470700-01-7
5'-O-benzyl-2'-deoxy-3'-O-diethylphosphoryl-4'α-{[(2-(2-iodophenyl)ethyl)thio]carbonyl}adenosine

Guidance literature:: Multi-step reaction with 6 steps

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

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

3: 95 percent / BOP-Cl; triethylamine / tetrahydrofuran; CH₂Cl₂ / 2 h / Heating

4: DMAP / CH₂Cl₂ / 0 °C

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

6: 88 percent / TMSOTf / CH₂Cl₂ / 0.83 h / 0 °C

With 2,6-dimethylpyridine; dmap; trimethylsilyl trifluoromethanesulfonate; 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:

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

: 470700-01-7
5'-O-benzyl-2'-deoxy-3'-O-diethylphosphoryl-4'α-{[(2-(2-iodophenyl)ethyl)thio]carbonyl}adenosine

Guidance literature:: Multi-step reaction with 4 steps

1: 95 percent / BOP-Cl; triethylamine / tetrahydrofuran; CH₂Cl₂ / 2 h / Heating

2: DMAP / CH₂Cl₂ / 0 °C

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

4: 88 percent / TMSOTf / CH₂Cl₂ / 0.83 h / 0 °C

With 2,6-dimethylpyridine; dmap; trimethylsilyl trifluoromethanesulfonate; iodine; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; In tetrahydrofuran; dichloromethane; water;
DOI:10.1016/S0040-4020(02)00557-4