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

Base Information

• Chemical Name: N⁴-benzoyl-5'-O-tert-butyldiphenylsilyl-4'-C-(p-toluenesulfonyl)oxymethylcytidine
• CAS No.: 446862-78-8
• Molecular Formula: C₄₀H₄₃N₃O₉SSi
• Molecular Weight: 769.948

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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

There total 11 articles about N⁴-benzoyl-5'-O-tert-butyldiphenylsilyl-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: 73.0%

N4-benzoyl-5'-O-tert-butyldiphenylsilyl-2',3'-di-O-acetyl-4'-C-(p-toluenesulfonyl)oxymethylcytidine (446862-77-7) → N4-benzoyl-5'-O-tert-butyldiphenylsilyl-4'-C-(p-toluenesulfonyl)oxymethylcytidine (446862-78-8)

Guidance literature:

With methanol; potassium carbonate; at 20 ℃; for 0.25h;

DOI:10.1039/a907218g

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → N4-benzoyl-5'-O-tert-butyldiphenylsilyl-4'-C-(p-toluenesulfonyl)oxymethylcytidine (446862-78-8)

Guidance literature:

Multi-step reaction with 5 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

5.1: 73 percent / K₂CO₃ / methanol / 0.25 h / 20 °C

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

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

Reference yield:

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3) → N4-benzoyl-5'-O-tert-butyldiphenylsilyl-4'-C-(p-toluenesulfonyl)oxymethylcytidine (446862-78-8)

Guidance literature:

Multi-step reaction with 5 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

5.1: 73 percent / K₂CO₃ / methanol / 0.25 h / 20 °C

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

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

upstream raw materials:

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

p-toluenesulfonyl chloride

tert-butylchlorodiphenylsilane

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

Downstream raw materials:

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

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