N⁴-benzoyl-5'-O-tert-butyldiphenylsilyl-2',3'-di-O-acetyl-4'-C-(p-toluenesulfonyl)oxymethylcytidine

Base Information

• Chemical Name: N⁴-benzoyl-5'-O-tert-butyldiphenylsilyl-2',3'-di-O-acetyl-4'-C-(p-toluenesulfonyl)oxymethylcytidine
• CAS No.: 446862-77-7
• Molecular Formula: C₄₄H₄₇N₃O₁₁SSi
• Molecular Weight: 854.022

Synonyms:N⁴-benzoyl-5'-O-tert-butyldiphenylsilyl-2',3'-di-O-acetyl-4'-C-(p-toluenesulfonyl)oxymethylcytidine

Chemical Property of N⁴-benzoyl-5'-O-tert-butyldiphenylsilyl-2',3'-di-O-acetyl-4'-C-(p-toluenesulfonyl)oxymethylcytidine

Chemical Property:

Purity/Quality:

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Technology Process of N⁴-benzoyl-5'-O-tert-butyldiphenylsilyl-2',3'-di-O-acetyl-4'-C-(p-toluenesulfonyl)oxymethylcytidine

There total 10 articles about N⁴-benzoyl-5'-O-tert-butyldiphenylsilyl-2',3'-di-O-acetyl-4'-C-(p-toluenesulfonyl)oxymethylcytidine 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: 82.0%

N4,O-bis(trimethylsilyl)-N4-benzoylcytosine (64339-87-3) + Acetic acid (2S,3S,4R)-4,5-diacetoxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester (260269-28-1) → N4-benzoyl-5'-O-tert-butyldiphenylsilyl-2',3'-di-O-acetyl-4'-C-(p-toluenesulfonyl)oxymethylcytidine (446862-77-7)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; Heating;

DOI:10.1039/a907218g

Reference yield: 82.0%

N4,O-bis(trimethylsilyl)-N4-benzoylcytosine (64339-87-3) + 5-O-tert-butyldiphenylsilyl-4-C-(p-toluenesulfonyl)oxymethyl-1,2,3-tri-O-acetyl-β-D-erythro-pentofuranose (446862-76-6) → N4-benzoyl-5'-O-tert-butyldiphenylsilyl-2',3'-di-O-acetyl-4'-C-(p-toluenesulfonyl)oxymethylcytidine (446862-77-7)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; for 5h; Heating;

DOI:10.1016/S0040-4020(02)00227-2

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → N4-benzoyl-5'-O-tert-butyldiphenylsilyl-2',3'-di-O-acetyl-4'-C-(p-toluenesulfonyl)oxymethylcytidine (446862-77-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 67 percent / CH₂Cl₂ / 11 h / 20 °C

2.1: 97 percent / 4,4-dimethylaminopyridine / CH₂Cl₂ / 16 h / 20 °C

3.1: conc. H₂SO₄ / acetic acid / 2 h / 20 °C

3.2: H₂ / 10 percent Pd/C / ethyl acetate; CHCl₃ / 16 h / 20 °C

3.3: pyridine / 49 h / 20 °C

4.1: 82 percent / trimethylsilyl trifluoromethanesulfonate / 1,2-dichloro-ethane / 5 h / Heating

With dmap; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; In dichloromethane; acetic acid; 1,2-dichloro-ethane;

DOI:10.1016/S0040-4020(02)00227-2

upstream raw materials:

N₄,O-bis(trimethylsilyl)-N₄-benzoylcytosine

Acetic acid (2S,3S,4R)-4,5-diacetoxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester

5-O-tert-butyldiphenylsilyl-4-C-(p-toluenesulfonyl)oxymethyl-1,2,3-tri-O-acetyl-β-D-erythro-pentofuranose

p-toluenesulfonyl chloride

Downstream raw materials:

N⁴-benzoyl-5'-O-tert-butyldiphenylsilyl-4'-C-(p-toluenesulfonyl)oxymethylcytidine

N⁴-benzoyl-5'-O-tert-butyldiphenylsilyl-3'-O,4'-C-methylenecytidine

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