5-Allyl-2'-deoxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-4-N-dimethylformamidine-6-oxocytidine

Base Information

• Chemical Name: 5-Allyl-2'-deoxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-4-N-dimethylformamidine-6-oxocytidine
• CAS No.: 294648-71-8
• Molecular Formula: C₃₆H₄₀N₄O₇
• Molecular Weight: 640.736

Synonyms:5-Allyl-2'-deoxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-4-N-dimethylformamidine-6-oxocytidine

Chemical Property of 5-Allyl-2'-deoxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-4-N-dimethylformamidine-6-oxocytidine

Chemical Property:

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Technology Process of 5-Allyl-2'-deoxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-4-N-dimethylformamidine-6-oxocytidine

There total 12 articles about 5-Allyl-2'-deoxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-4-N-dimethylformamidine-6-oxocytidine 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: 86.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + 5-Allyl-2'-deoxy-4-N-dimethylformamidine-6-oxocytidine (294648-63-8) → 5-Allyl-2'-deoxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-4-N-dimethylformamidine-6-oxocytidine (294648-71-8)

Guidance literature:

With pyridine; at -40 - 20 ℃; for 8h;

DOI:10.1002/1521-3765(20000703)6:13<2409::AID-CHEM2409>3.0.CO;2-H

Reference yield:

6-Oxocytidine (150439-90-0) → 5-Allyl-2'-deoxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-4-N-dimethylformamidine-6-oxocytidine (294648-71-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 37 percent / Et₃N / Pd(PPh₃)4 / dimethylformamide / 21.5 h / 20 - 70 °C

2: 88 percent / methanol / 0.17 h / Heating

3: 88 percent / pyridine / 1,2-dichloro-ethane / 3 h / 0 - 20 °C

4: 52 percent / DMAP / acetonitrile / 4 h / 20 °C

5: 58 percent / AIBN; nBu₃SnH / toluene / 1.5 h / 75 °C

6: 98 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

7: 86 percent / pyridine / 8 h / -40 - 20 °C

With pyridine; dmap; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile; 1: Alkylation / 2: Condensation / 3: Substitution / 4: Substitution / 5: Reduction / 6: Substitution / 7: Substitution;

DOI:10.1002/1521-3765(20000703)6:13<2409::AID-CHEM2409>3.0.CO;2-H

Reference yield:

2',3',5'-Tri-O-acetyl-6-oxocytidine (23526-06-9) → 5-Allyl-2'-deoxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-4-N-dimethylformamidine-6-oxocytidine (294648-71-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 93 percent / NH₃ / methanol / 24 h / 20 °C

2: 37 percent / Et₃N / Pd(PPh₃)4 / dimethylformamide / 21.5 h / 20 - 70 °C

3: 88 percent / methanol / 0.17 h / Heating

4: 88 percent / pyridine / 1,2-dichloro-ethane / 3 h / 0 - 20 °C

5: 52 percent / DMAP / acetonitrile / 4 h / 20 °C

6: 58 percent / AIBN; nBu₃SnH / toluene / 1.5 h / 75 °C

7: 98 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

8: 86 percent / pyridine / 8 h / -40 - 20 °C

With pyridine; dmap; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; ammonia; tri-n-butyl-tin hydride; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile; 1: Deacetylation / 2: Alkylation / 3: Condensation / 4: Substitution / 5: Substitution / 6: Reduction / 7: Substitution / 8: Substitution;

DOI:10.1002/1521-3765(20000703)6:13<2409::AID-CHEM2409>3.0.CO;2-H

upstream raw materials:

4,4'-dimethoxytrityl chloride

5-Allyl-2'-deoxy-4-N-dimethylformamidine-6-oxocytidine

6-Oxocytidine

2',3',5'-Tri-O-acetyl-6-oxocytidine

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