5'-O-(monomethoxytrityl)thymidylyl-{3'-{O^P-[2-(5-phenylpyrimidin-2-yl)ethyl]}-5'}-3'-O-acethylthymidine

Base Information

• Chemical Name: 5'-O-(monomethoxytrityl)thymidylyl-{3'-{O^P-[2-(5-phenylpyrimidin-2-yl)ethyl]}-5'}-3'-O-acethylthymidine
• CAS No.: 322733-16-4
• Molecular Formula: C₅₄H₅₅N₆O₁₄P
• Molecular Weight: 1043.04

Synonyms:5'-O-(monomethoxytrityl)thymidylyl-{3'-{O^P-[2-(5-phenylpyrimidin-2-yl)ethyl]}-5'}-3'-O-acethylthymidine

Chemical Property of 5'-O-(monomethoxytrityl)thymidylyl-{3'-{O^P-[2-(5-phenylpyrimidin-2-yl)ethyl]}-5'}-3'-O-acethylthymidine

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Technology Process of 5'-O-(monomethoxytrityl)thymidylyl-{3'-{O^P-[2-(5-phenylpyrimidin-2-yl)ethyl]}-5'}-3'-O-acethylthymidine

There total 4 articles about 5'-O-(monomethoxytrityl)thymidylyl-{3'-{O^P-[2-(5-phenylpyrimidin-2-yl)ethyl]}-5'}-3'-O-acethylthymidine 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: 67.0%

3'-O-acetylthymidine (21090-30-2) + 5'-O-(monomethoxytrityl)thymidine 3'-[2-(5-phenylpyrimidin-2-yl)ethyl triethylammonium phosphate] → 5'-O-(monomethoxytrityl)thymidylyl-{3'-{OP-[2-(5-phenylpyrimidin-2-yl)ethyl]}-5'}-3'-O-acethylthymidine (322733-16-4)

Guidance literature:

With 1-methyl-1H-imidazole; Triphenylsilyl chloride; In pyridine; at 20 ℃; for 24h;

DOI:10.1002/1522-2675(20001108)83:11<3053::AID-HLCA3053>3.0.CO;2-X

Reference yield:

3-(dimethylamino)-2-phenylacrylaldehyde (85907-55-7) → 5'-O-(monomethoxytrityl)thymidylyl-{3'-{OP-[2-(5-phenylpyrimidin-2-yl)ethyl]}-5'}-3'-O-acethylthymidine (322733-16-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: Na / ethanol / 0.5 h

1.2: 6 h / Heating

2.1: 1,2,4-1H-triazole / pyridine / 0.5 h / 0 °C

2.2: pyridine / 1 h

2.3: 91 percent / pyridine / 24 h

3.1: 4-nitrobenzaldehyde oxime / dioxane; H₂O / 0.17 h / 20 °C

3.2: 98 percent / dioxane; H₂O / 2.5 h

4.1: 67 percent / 1-methyl-1H-imidazole; TPS-Cl / pyridine / 24 h / 20 °C

With 1,2,4-Triazole; 1-methyl-1H-imidazole; Triphenylsilyl chloride; sodium; 4-nitrobenzaldehyde oxime; In 1,4-dioxane; pyridine; ethanol; water;

DOI:10.1002/1522-2675(20001108)83:11<3053::AID-HLCA3053>3.0.CO;2-X

Reference yield:

5-phenylpyrimidine-2-ethanol (53868-59-0) → 5'-O-(monomethoxytrityl)thymidylyl-{3'-{OP-[2-(5-phenylpyrimidin-2-yl)ethyl]}-5'}-3'-O-acethylthymidine (322733-16-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1,2,4-1H-triazole / pyridine / 0.5 h / 0 °C

1.2: pyridine / 1 h

1.3: 91 percent / pyridine / 24 h

2.1: 4-nitrobenzaldehyde oxime / dioxane; H₂O / 0.17 h / 20 °C

2.2: 98 percent / dioxane; H₂O / 2.5 h

3.1: 67 percent / 1-methyl-1H-imidazole; TPS-Cl / pyridine / 24 h / 20 °C

With 1,2,4-Triazole; 1-methyl-1H-imidazole; Triphenylsilyl chloride; 4-nitrobenzaldehyde oxime; In 1,4-dioxane; pyridine; water;

DOI:10.1002/1522-2675(20001108)83:11<3053::AID-HLCA3053>3.0.CO;2-X

upstream raw materials:

3'-O-acetylthymidine

3-(dimethylamino)-2-phenylacrylaldehyde

5-phenylpyrimidine-2-ethanol

5'-O-(monomethoxytrityl)thymidine 3'-[2,5-dichlorophenyl 2-(5-phenylpyrimidin-2-yl)ethyl phosphate]

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