N-benzoyI-1-[S-(4,4'-dimethoxytrityl)-3-(t-butyIdimethylsilyl)-4-thio-β-D-ribofuranosyl]cytosine

Base Information

• Chemical Name: N-benzoyI-1-[S-(4,4'-dimethoxytrityl)-3-(t-butyIdimethylsilyl)-4-thio-β-D-ribofuranosyl]cytosine
• CAS No.: 159981-13-2
• Molecular Formula: C₄₃H₄₉N₃O₇SSi
• Molecular Weight: 780.029
• Mol file: 159981-13-2.mol

Synonyms:N-benzoyI-1-[S-(4,4'-dimethoxytrityl)-3-(t-butyIdimethylsilyl)-4-thio-β-D-ribofuranosyl]cytosine

Chemical Property of N-benzoyI-1-[S-(4,4'-dimethoxytrityl)-3-(t-butyIdimethylsilyl)-4-thio-β-D-ribofuranosyl]cytosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-benzoyI-1-[S-(4,4'-dimethoxytrityl)-3-(t-butyIdimethylsilyl)-4-thio-β-D-ribofuranosyl]cytosine

There total 5 articles about N-benzoyI-1-[S-(4,4'-dimethoxytrityl)-3-(t-butyIdimethylsilyl)-4-thio-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: 51.3%

tert-butyldimethylsilyl chloride (18162-48-6) + N4-benzoyl-1-[5-O-(4,4'-dimethoxytrityl)-4-thio-β-D-ribofuranosyl]cytosine (159981-09-6) → N-benzoyI-1-[S-(4,4'-dimethoxytrityl)-3-(t-butyIdimethylsilyl)-4-thio-β-D-ribofuranosyl]cytosine (159981-13-2) + N4-benzoyl-1-[2-O-(tert-butyldimethylsilyl)-5-O-(4,4'-dimethoxytrityl)-4-thio-β-D-ribofuranosyl]cytosine (159981-11-0)

Guidance literature:

N⁴-benzoyl-1-[5-O-(4,4'-dimethoxytrityl)-4-thio-β-D-ribofuranosyl]cytosine; With pyridine; silver nitrate; In tetrahydrofuran; at 20 ℃; for 0.5h;

tert-butyldimethylsilyl chloride; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/jm050822c

Reference yield:

1-[5-(4,4'-dimethoxytrityl)-3-(t-butyldimethylsilyl)-4-thio-beta-D-ribofuranosyl]uracil (149359-06-8) → N-benzoyI-1-[S-(4,4'-dimethoxytrityl)-3-(t-butyIdimethylsilyl)-4-thio-β-D-ribofuranosyl]cytosine (159981-13-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: imidazole; pyridine / 24 h / 20 °C

2.1: 1,2,4-triazole; POCl₃; Et₃N / acetonitrile / 20 °C

2.2: aq. NH₃ / dioxane

3.1: pyridine

4.1: 13 g / triethylamine trihydrofluoride; triethylamine / tetrahydrofuran / 20 °C

5.1: pyridine; AgNO₃ / tetrahydrofuran / 0.5 h / 20 °C

5.2: 47 percent / tetrahydrofuran / 20 °C

With pyridine; 1H-imidazole; 1,2,4-Triazole; triethylamine trihydrofluoride; silver nitrate; triethylamine; trichlorophosphate; In tetrahydrofuran; acetonitrile;

DOI:10.1021/jm050822c

Reference yield:

1-[2,3-O-bis(tert-butyldimethylsilyl)-5-O-(4,4'-dimethoxytrityl)-4-thio-β-D-ribofuranosyl]uracil (848649-47-8) → N-benzoyI-1-[S-(4,4'-dimethoxytrityl)-3-(t-butyIdimethylsilyl)-4-thio-β-D-ribofuranosyl]cytosine (159981-13-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 1,2,4-triazole; POCl₃; Et₃N / acetonitrile / 20 °C

1.2: aq. NH₃ / dioxane

2.1: pyridine

3.1: 13 g / triethylamine trihydrofluoride; triethylamine / tetrahydrofuran / 20 °C

4.1: pyridine; AgNO₃ / tetrahydrofuran / 0.5 h / 20 °C

4.2: 47 percent / tetrahydrofuran / 20 °C

With pyridine; 1,2,4-Triazole; triethylamine trihydrofluoride; silver nitrate; triethylamine; trichlorophosphate; In tetrahydrofuran; acetonitrile;

DOI:10.1021/jm050822c

upstream raw materials:

tert-butyldimethylsilyl chloride

N⁴-benzoyl-1-[5-O-(4,4'-dimethoxytrityl)-4-thio-β-D-ribofuranosyl]cytosine

1-[5-(4,4'-dimethoxytrityl)-3-(t-butyldimethylsilyl)-4-thio-beta-D-ribofuranosyl]uracil

1-[2,3-O-bis(tert-butyldimethylsilyl)-5-O-(4,4'-dimethoxytrityl)-4-thio-β-D-ribofuranosyl]uracil

Downstream raw materials:

N⁴-benzoyl-1-[2-O-(tert-butyldimethylsilyl)-3-O-[(2-cyanoethyl)(N,N-diisopropylamino)phosphino]-5-O-(4,4'-dimethoxytrityl)-4-thio-β-D-ribofuranosyl]cytosine

N⁴-benzoyl-1-[2-O-(tert-butyldimethylsilyl)-5-O-(4,4'-dimethoxytrityl)-4-thio-β-D-ribofuranosyl]cytosine