N⁴-benzoyl-1-[2-O-(tert-butyldimethylsilyl)-3-deoxy-3-α-(ethoxycarbonyl)methyl-β-D-ribofuranosyl]cytosine

Base Information

• Chemical Name: N⁴-benzoyl-1-[2-O-(tert-butyldimethylsilyl)-3-deoxy-3-α-(ethoxycarbonyl)methyl-β-D-ribofuranosyl]cytosine
• CAS No.: 265331-08-6
• Molecular Formula: C₂₆H₃₇N₃O₇Si
• Molecular Weight: 531.681

Synonyms:N⁴-benzoyl-1-[2-O-(tert-butyldimethylsilyl)-3-deoxy-3-α-(ethoxycarbonyl)methyl-β-D-ribofuranosyl]cytosine

Chemical Property of N⁴-benzoyl-1-[2-O-(tert-butyldimethylsilyl)-3-deoxy-3-α-(ethoxycarbonyl)methyl-β-D-ribofuranosyl]cytosine

Chemical Property:

Purity/Quality:

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Technology Process of N⁴-benzoyl-1-[2-O-(tert-butyldimethylsilyl)-3-deoxy-3-α-(ethoxycarbonyl)methyl-β-D-ribofuranosyl]cytosine

There total 5 articles about N⁴-benzoyl-1-[2-O-(tert-butyldimethylsilyl)-3-deoxy-3-α-(ethoxycarbonyl)methyl-β-D-ribofuranosyl]cytosine 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: 52.0%

N4-benzoyl-1-[2,5-bis-O-(tert-butyldimethylsilyl)-3-deoxy-3-α-(ethoxycarbonyl)methyl-β-D-ribofuranosyl]cytosine (265331-07-5) → N4-benzoyl-1-[2-O-(tert-butyldimethylsilyl)-3-deoxy-3-α-(ethoxycarbonyl)methyl-β-D-ribofuranosyl]cytosine (265331-08-6)

Guidance literature:

With camphor-10-sulfonic acid; In methanol; at 20 ℃;

DOI:10.1002/(sici)1099-0690(200002)2000:4<633::aid-ejoc633>3.0.co;2-u

Reference yield:

2',5'-bis-O-tert-butyldimethylsilyl-3'-ketouridine (90813-54-0) → N4-benzoyl-1-[2-O-(tert-butyldimethylsilyl)-3-deoxy-3-α-(ethoxycarbonyl)methyl-β-D-ribofuranosyl]cytosine (265331-08-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 65 percent / tetrahydrofuran / 18 h / 20 °C

2: 92 percent / H₂ / 10percent Pd/C / ethanol / 16 h

3: 76.5 percent / POCl₃; Et₃N / acetonitrile / 18 h / 20 °C

4: 91 percent / NaH (60percent w/w) / dioxane / 1.5 h

5: 52 percent / camphorsulfonic acid / methanol / 20 °C

With camphor-10-sulfonic acid; hydrogen; triethylamine; trichlorophosphate; 10percent Pd/C; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; acetonitrile; 1: Wittig reaction / 2: Catalytic hydrogenation / 3: Condensation / 4: Substitution / 5: Hydrolysis;

DOI:10.1002/(sici)1099-0690(200002)2000:4<633::aid-ejoc633>3.0.co;2-u

Reference yield:

1-[2,5-bis-O-(tert-butyldimethylsilyl)-3-deoxy-3-(ethoxycarbonyl)methylene-β-D-ribofuranosyl]uracil (251296-54-5) → N4-benzoyl-1-[2-O-(tert-butyldimethylsilyl)-3-deoxy-3-α-(ethoxycarbonyl)methyl-β-D-ribofuranosyl]cytosine (265331-08-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / H₂ / 10percent Pd/C / ethanol / 16 h

2: 76.5 percent / POCl₃; Et₃N / acetonitrile / 18 h / 20 °C

3: 91 percent / NaH (60percent w/w) / dioxane / 1.5 h

4: 52 percent / camphorsulfonic acid / methanol / 20 °C

With camphor-10-sulfonic acid; hydrogen; triethylamine; trichlorophosphate; 10percent Pd/C; In 1,4-dioxane; methanol; ethanol; acetonitrile; 1: Catalytic hydrogenation / 2: Condensation / 3: Substitution / 4: Hydrolysis;

DOI:10.1002/(sici)1099-0690(200002)2000:4<633::aid-ejoc633>3.0.co;2-u

upstream raw materials:

N⁴-benzoyl-1-[2,5-bis-O-(tert-butyldimethylsilyl)-3-deoxy-3-α-(ethoxycarbonyl)methyl-β-D-ribofuranosyl]cytosine

2',5'-bis-O-tert-butyldimethylsilyl-3'-ketouridine

1-[2,5-bis-O-(tert-butyldimethylsilyl)-3-deoxy-3-(ethoxycarbonyl)methylene-β-D-ribofuranosyl]uracil

1-[2,5-bis-O-(tert-butyldimethylsilyl)-3-deoxy-3-α-(ethoxycarbonyl)methyl-β-D-ribofuranosyl]uracil

Downstream raw materials:

N⁴-benzoyl-1-[2-O-(tert-butyldimethylsilyl)-3-deoxy-3-α-(ethoxycarbonyl)methyl-5-O-(dimethoxytrityl)-β-D-ribofuranosyl]cytosine

N⁴-benzoyl-1-[2-O-(tert-butyldimethylsilyl)-3-α-(carboxy)methyl-3-deoxy-5-O-(dimethoxytrityl)-β-D-ribofuranosyl]cytosine

N⁴-benzoyl-1-{2-O-(tert-butyldimethylsilyl)-3-deoxy-5-O-(dimethoxytrityl)-3-α-[N-(5'-deoxythymidin-5'-yl)carboxamido]methyl-β-D-ribofuranosyl}cytosine

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