Thymidine-3'-O-<β-cyanoethyl-(S-2,4-dichlorobenzyl)>-phosphorodithioate

Base Information

• Chemical Name: Thymidine-3'-O-<β-cyanoethyl-(S-2,4-dichlorobenzyl)>-phosphorodithioate
• CAS No.: 129789-69-1
• Molecular Formula: C₂₀H₂₂Cl₂N₃O₆PS₂
• Molecular Weight: 566.423

Synonyms:Thymidine-3'-O-<β-cyanoethyl-(S-2,4-dichlorobenzyl)>-phosphorodithioate

Chemical Property of Thymidine-3'-O-<β-cyanoethyl-(S-2,4-dichlorobenzyl)>-phosphorodithioate

Chemical Property:

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Technology Process of Thymidine-3'-O-<β-cyanoethyl-(S-2,4-dichlorobenzyl)>-phosphorodithioate

There total 3 articles about Thymidine-3'-O-<β-cyanoethyl-(S-2,4-dichlorobenzyl)>-phosphorodithioate 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: 80.0%

5'-O-Dimethoxytritylthymidine-3'-O-[β-cyanoethyl-(S-2,4-dichlorobenzyl)]-phosphorodithioate (129789-64-6) → Thymidine-3'-O-<β-cyanoethyl-(S-2,4-dichlorobenzyl)>-phosphorodithioate (129789-69-1)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; dichloromethane; at 0 ℃;

DOI:10.1016/S0040-4039(00)88887-5

Reference yield:

5'-O-(4,4'-dimethoxytrityl)-2'-deoxythymidine-3'-O-[O-(2-cyanoethyl)-N,N'-diisopropylphosphoramidite] (98796-51-1) → Thymidine-3'-O-<β-cyanoethyl-(S-2,4-dichlorobenzyl)>-phosphorodithioate (129789-69-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) tetrazole, 2) sulfur, 2,6-lutidine / 1) CH₃CN, 40 min, 2) toluene, 1 h, rt

2: 80 percent / 2percent p-toluenesulfonic acid / CH₂Cl₂; methanol / 0 °C

With 2,6-dimethylpyridine; 1H-tetrazole; toluene-4-sulfonic acid; sulfur; In methanol; dichloromethane;

DOI:10.1016/S0040-4039(00)88887-5

Reference yield:

2,4-dichlorobenzyl mercaptan (59293-67-3) → Thymidine-3'-O-<β-cyanoethyl-(S-2,4-dichlorobenzyl)>-phosphorodithioate (129789-69-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) tetrazole, 2) sulfur, 2,6-lutidine / 1) CH₃CN, 40 min, 2) toluene, 1 h, rt

2: 80 percent / 2percent p-toluenesulfonic acid / CH₂Cl₂; methanol / 0 °C

With 2,6-dimethylpyridine; 1H-tetrazole; toluene-4-sulfonic acid; sulfur; In methanol; dichloromethane;

DOI:10.1016/S0040-4039(00)88887-5

upstream raw materials:

5'-O-Dimethoxytritylthymidine-3'-O-[β-cyanoethyl-(S-2,4-dichlorobenzyl)]-phosphorodithioate

5'-O-(4,4'-dimethoxytrityl)-2'-deoxythymidine-3'-O-[O-(2-cyanoethyl)-N,N'-diisopropylphosphoramidite]

2,4-dichlorobenzyl mercaptan

Downstream raw materials:

C₅₈H₅₇Cl₄N₅O₁₃P₂S₄

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