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

Base Information

• Chemical Name: 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
• CAS No.: 265331-11-1
• Molecular Formula: C₅₅H₆₄N₆O₁₂Si
• Molecular Weight: 1029.23

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 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

There total 8 articles about 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 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: 74.0%

5'-amino-5'-deoxythymidine (25152-20-9) + N4-benzoyl-1-[2-O-(tert-butyldimethylsilyl)-3-α-(carboxy)methyl-3-deoxy-5-O-(dimethoxytrityl)-β-D-ribofuranosyl]cytosine (265331-10-0) → 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 (265331-11-1)

Guidance literature:

With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; In tetrahydrofuran; acetonitrile;

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-5-O-(dimethoxytrityl)-3-α-[N-(5'-deoxythymidin-5'-yl)carboxamido]methyl-β-D-ribofuranosyl}cytosine (265331-11-1)

Guidance literature:

Multi-step reaction with 8 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

6: 77 percent / pyridine / 20 °C

7: 37 percent / 10percent NaOH / aq. ethanol / 3 h / 20 °C

8: 74 percent / HBTU; 1-hydroxybenzotriazole; Et₃N / acetonitrile; tetrahydrofuran

With camphor-10-sulfonic acid; hydrogen; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; trichlorophosphate; 10percent Pd/C; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; ethanol; acetonitrile; 1: Wittig reaction / 2: Catalytic hydrogenation / 3: Condensation / 4: Substitution / 5: Hydrolysis / 6: Etherification / 7: saponification / 8: Condensation;

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-5-O-(dimethoxytrityl)-3-α-[N-(5'-deoxythymidin-5'-yl)carboxamido]methyl-β-D-ribofuranosyl}cytosine (265331-11-1)

Guidance literature:

Multi-step reaction with 7 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

5: 77 percent / pyridine / 20 °C

6: 37 percent / 10percent NaOH / aq. ethanol / 3 h / 20 °C

7: 74 percent / HBTU; 1-hydroxybenzotriazole; Et₃N / acetonitrile; tetrahydrofuran

With camphor-10-sulfonic acid; hydrogen; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; trichlorophosphate; 10percent Pd/C; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; ethanol; acetonitrile; 1: Catalytic hydrogenation / 2: Condensation / 3: Substitution / 4: Hydrolysis / 5: Etherification / 6: saponification / 7: Condensation;

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

upstream raw materials:

5'-amino-5'-deoxythymidine

N⁴-benzoyl-1-[2-O-(tert-butyldimethylsilyl)-3-α-(carboxy)methyl-3-deoxy-5-O-(dimethoxytrityl)-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

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