Cytidine, N-benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-O-[(1,1-dimethyl ethyl)dimethylsilyl]-4'-thio-, 3'-[2-cyanoethyl bis(1-methylethyl)phosphoramidite]

Base Information

• Chemical Name: Cytidine, N-benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-O-[(1,1-dimethyl ethyl)dimethylsilyl]-4'-thio-, 3'-[2-cyanoethyl bis(1-methylethyl)phosphoramidite]
• CAS No.: 172531-76-9
• Molecular Formula: C52H66N5O8PSSi
• Molecular Weight: 980.25
• Mol file: 172531-76-9.mol

Synonyms:

Chemical Property of Cytidine, N-benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-O-[(1,1-dimethyl ethyl)dimethylsilyl]-4'-thio-, 3'-[2-cyanoethyl bis(1-methylethyl)phosphoramidite]

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Cytidine, N-benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-O-[(1,1-dimethyl ethyl)dimethylsilyl]-4'-thio-, 3'-[2-cyanoethyl bis(1-methylethyl)phosphoramidite]

There total 9 articles about Cytidine, N-benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-O-[(1,1-dimethyl ethyl)dimethylsilyl]-4'-thio-, 3'-[2-cyanoethyl bis(1-methylethyl)phosphoramidite] 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: 94.0%

N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite (102691-36-1) + N4-benzoyl-1-[2-O-(tert-butyldimethylsilyl)-5-O-(4,4'-dimethoxytrityl)-4-thio-β-D-ribofuranosyl]cytosine (159981-11-0) → 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 (172531-76-9)

Guidance literature:

With 1-methyl-1H-imidazole; 1H-tetrazole; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/jm050822c

Reference yield: 89.0%

2-cyanoethoxy-N,N,N',N'-tetraisopropylphosphoramidite + N4-benzoyl-1-[2-O-(tert-butyldimethylsilyl)-5-O-(4,4'-dimethoxytrityl)-4-thio-β-D-ribofuranosyl]cytosine (159981-11-0) → 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 (172531-76-9)

Guidance literature:

With 1-methyl-1H-imidazole; 1H-tetrazole; In DMF (N,N-dimethyl-formamide); at 20 ℃; for 8h;

Reference yield:

1-[5-(4,4'-dimethoxytrityl)-3-(t-butyldimethylsilyl)-4-thio-beta-D-ribofuranosyl]uracil (149359-06-8) → 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 (172531-76-9)

Guidance literature:

Multi-step reaction with 7 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

6.1: Et₃N; imidazole / ethanol

7.1: 94 percent / tetrazole; N-methylimidazole / dimethylformamide / 20 °C

With pyridine; 1H-imidazole; 1,2,4-Triazole; 1-methyl-1H-imidazole; 1H-tetrazole; triethylamine trihydrofluoride; silver nitrate; triethylamine; trichlorophosphate; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm050822c

upstream raw materials:

N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite

N⁴-benzoyl-1-[2-O-(tert-butyldimethylsilyl)-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