3',5'-bis-O-(tert-butyldimethylsilyl)-O⁴-[(2,4,6-trimethylphenyl)sulfonyl]thymidine

Base Information

• Chemical Name: 3',5'-bis-O-(tert-butyldimethylsilyl)-O⁴-[(2,4,6-trimethylphenyl)sulfonyl]thymidine
• CAS No.: 947251-79-8
• Molecular Formula: C₃₁H₅₂N₂O₇SSi₂
• Molecular Weight: 653

Synonyms:3',5'-bis-O-(tert-butyldimethylsilyl)-O⁴-[(2,4,6-trimethylphenyl)sulfonyl]thymidine

Chemical Property of 3',5'-bis-O-(tert-butyldimethylsilyl)-O⁴-[(2,4,6-trimethylphenyl)sulfonyl]thymidine

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

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Technology Process of 3',5'-bis-O-(tert-butyldimethylsilyl)-O⁴-[(2,4,6-trimethylphenyl)sulfonyl]thymidine

There total 4 articles about 3',5'-bis-O-(tert-butyldimethylsilyl)-O⁴-[(2,4,6-trimethylphenyl)sulfonyl]thymidine 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: 89.0%

2-mesitylenesulphonyl chloride (773-64-8) + 3',5'-O-di(tert-butyldimethylsilyl)thymidine (40733-26-4) → 3',5'-bis-O-(tert-butyldimethylsilyl)-O4-[(2,4,6-trimethylphenyl)sulfonyl]thymidine (947251-79-8)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 31h;

DOI:10.1021/jo070843+

Reference yield: 15.0%

2-mesitylenesulphonyl chloride (773-64-8) + 3',5'-O-di(tert-butyldimethylsilyl)thymidine (40733-26-4) → 3',5'-bis-O-(tert-butyldimethylsilyl)-O4-[(2,4,6-trimethylphenyl)sulfonyl]thymidine (947251-79-8) + C31H52N2O7Si2S

Guidance literature:

With sodium hydride; In tetrahydrofuran;

DOI:10.1021/jo070843+

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 3',5'-bis-O-(tert-butyldimethylsilyl)-O4-[(2,4,6-trimethylphenyl)sulfonyl]thymidine (947251-79-8)

Guidance literature:

Multi-step reaction with 2 steps

1: imidazole / dimethylformamide / 24 h / 20 °C

2: 89 percent / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 31 h / 0 - 20 °C

With 1H-imidazole; dmap; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo070843+

upstream raw materials:

2-mesitylenesulphonyl chloride

3',5'-O-di(tert-butyldimethylsilyl)thymidine

tert-butyldimethylsilyl chloride

thymidine

Downstream raw materials:

1-[3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyribofuranosyl]-4-(4-methoxyphenyl)-5-methylpyrimidin-2(1H)-one

3',5'-O-di(tert-butyldimethylsilyl)thymidine

1-[3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyribofuranosyl]-4-(3-methoxyphenyl)-5-methylpyrimidin-2(1H)-one

1-[3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyribofuranosyl]-4-(4-acetylphenyl)-5-methylpyrimidin-2(1H)-one

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