3'-O-methylene-5'-deoxy-5'-thiothymidylyl-(3'->5')-N⁶-benzoyl-3'-O-tert-butyldimethylsilyl-2',5'-dideoxy-5'-thioadenosine

Base Information

• Chemical Name: 3'-O-methylene-5'-deoxy-5'-thiothymidylyl-(3'->5')-N⁶-benzoyl-3'-O-tert-butyldimethylsilyl-2',5'-dideoxy-5'-thioadenosine
• CAS No.: 174523-26-3
• Molecular Formula: C₃₄H₄₅N₇O₇S₂Si
• Molecular Weight: 755.991

Synonyms:3'-O-methylene-5'-deoxy-5'-thiothymidylyl-(3'->5')-N⁶-benzoyl-3'-O-tert-butyldimethylsilyl-2',5'-dideoxy-5'-thioadenosine

Chemical Property of 3'-O-methylene-5'-deoxy-5'-thiothymidylyl-(3'->5')-N⁶-benzoyl-3'-O-tert-butyldimethylsilyl-2',5'-dideoxy-5'-thioadenosine

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Technology Process of 3'-O-methylene-5'-deoxy-5'-thiothymidylyl-(3'->5')-N⁶-benzoyl-3'-O-tert-butyldimethylsilyl-2',5'-dideoxy-5'-thioadenosine

There total 10 articles about 3'-O-methylene-5'-deoxy-5'-thiothymidylyl-(3'->5')-N⁶-benzoyl-3'-O-tert-butyldimethylsilyl-2',5'-dideoxy-5'-thioadenosine 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: 49.0%

5'-S-acetyl-3'-O-methylene-5'-deoxy-5'-thiothymidylyl-(3'->5')-N6-benzoyl-3'-O-tert-butyldimethylsilyl-2',5'-dideoxy-5'-thioadenosine (174523-22-9) → 3'-O-methylene-5'-deoxy-5'-thiothymidylyl-(3'->5')-N6-benzoyl-3'-O-tert-butyldimethylsilyl-2',5'-dideoxy-5'-thioadenosine (174523-26-3)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; methanol; at 0 ℃; for 1h;

DOI:10.1139/cjc-77-8-1410

Reference yield:

5'-O-(4,4'-dimethoxytrityl)-3'-O-(methylthiomethyl)thymidine (129185-32-6) → 3'-O-methylene-5'-deoxy-5'-thiothymidylyl-(3'->5')-N6-benzoyl-3'-O-tert-butyldimethylsilyl-2',5'-dideoxy-5'-thioadenosine (174523-26-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / p-TsOH*H₂O / methanol; CH₂Cl₂ / 0.25 h / 0 °C

2: 96 percent / diisopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 1.83 h / 0 - 20 °C

3: SO₂Cl₂; N,N-diisopropylethylamine / CH₂Cl₂ / 0.03 h / 0 °C

4: N,N-diisopropylethylamine / CH₂Cl₂ / 3.5 h

5: 49 percent / 1 N aq. NaOH / methanol; tetrahydrofuran / 1 h / 0 °C

With sodium hydroxide; sulfuryl dichloride; di-isopropyl azodicarboxylate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; 1: acidolysis / 2: Mitsunobu coupling / 3: Chlorination / 4: Condensation / 5: Hydrolysis;

DOI:10.1139/cjc-77-8-1410

Reference yield:

3'-O-(methylthiomethyl)thymidine (133510-56-2) → 3'-O-methylene-5'-deoxy-5'-thiothymidylyl-(3'->5')-N6-benzoyl-3'-O-tert-butyldimethylsilyl-2',5'-dideoxy-5'-thioadenosine (174523-26-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / diisopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 1.83 h / 0 - 20 °C

2: SO₂Cl₂; N,N-diisopropylethylamine / CH₂Cl₂ / 0.03 h / 0 °C

3: N,N-diisopropylethylamine / CH₂Cl₂ / 3.5 h

4: 49 percent / 1 N aq. NaOH / methanol; tetrahydrofuran / 1 h / 0 °C

With sodium hydroxide; sulfuryl dichloride; di-isopropyl azodicarboxylate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; 1: Mitsunobu coupling / 2: Chlorination / 3: Condensation / 4: Hydrolysis;

DOI:10.1139/cjc-77-8-1410

upstream raw materials:

5'-S-acetyl-3'-O-methylene-5'-deoxy-5'-thiothymidylyl-(3'->5')-N⁶-benzoyl-3'-O-tert-butyldimethylsilyl-2',5'-dideoxy-5'-thioadenosine

5'-O-(4,4'-dimethoxytrityl)-3'-O-(methylthiomethyl)thymidine

3'-O-(methylthiomethyl)thymidine

tert-butyldimethylsilyl chloride

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