N⁴-benzoyl-1-<3-O-(tert-butyldimethylsilyl)-5-O-(tert-butyldiphenylsilyl)-2-deoxy-4α-iodomethyl-β-D-ribo-pentofuranosyl>cytosine

Base Information

• Chemical Name: N⁴-benzoyl-1-<3-O-(tert-butyldimethylsilyl)-5-O-(tert-butyldiphenylsilyl)-2-deoxy-4α-iodomethyl-β-D-ribo-pentofuranosyl>cytosine
• CAS No.: 232588-83-9
• Molecular Formula: C₃₉H₅₀IN₃O₅Si₂
• Molecular Weight: 823.919

Synonyms:N⁴-benzoyl-1-<3-O-(tert-butyldimethylsilyl)-5-O-(tert-butyldiphenylsilyl)-2-deoxy-4α-iodomethyl-β-D-ribo-pentofuranosyl>cytosine

Chemical Property of N⁴-benzoyl-1-<3-O-(tert-butyldimethylsilyl)-5-O-(tert-butyldiphenylsilyl)-2-deoxy-4α-iodomethyl-β-D-ribo-pentofuranosyl>cytosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N⁴-benzoyl-1-<3-O-(tert-butyldimethylsilyl)-5-O-(tert-butyldiphenylsilyl)-2-deoxy-4α-iodomethyl-β-D-ribo-pentofuranosyl>cytosine

There total 10 articles about N⁴-benzoyl-1-<3-O-(tert-butyldimethylsilyl)-5-O-(tert-butyldiphenylsilyl)-2-deoxy-4α-iodomethyl-β-D-ribo-pentofuranosyl>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: 70.0%

N4-benzoyl-1-<3-O-(tert-butyldimethylsilyl)-5-O-(tert-butyldiphenylsilyl)-2-deoxy-4α-hydroxymethyl-β-D-ribo-pentofuranosyl>cytosine (232588-75-9) → N4-benzoyl-1-<3-O-(tert-butyldimethylsilyl)-5-O-(tert-butyldiphenylsilyl)-2-deoxy-4α-iodomethyl-β-D-ribo-pentofuranosyl>cytosine (232588-83-9)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In benzene; at 80 ℃; for 30h;

DOI:10.1021/jm990050i

Reference yield:

N4-Benzoyl-5'-O-(dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-2'-deoxycytidine (93134-40-8) → N4-benzoyl-1-<3-O-(tert-butyldimethylsilyl)-5-O-(tert-butyldiphenylsilyl)-2-deoxy-4α-iodomethyl-β-D-ribo-pentofuranosyl>cytosine (232588-83-9)

Guidance literature:

Multi-step reaction with 7 steps

1: TFA / CH₂Cl₂ / 2 h / Ambient temperature

2: 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, DMSO / benzene / 0.5 h / Ambient temperature

3: 1.) 2 M NaOH, 2.) NaBH₄ / 1.) 1,4-dioxane, water, RT, 10 min, 2.) EtOH, 0 deg C, 20 min

4: pyridine / 0.83 h / Ambient temperature

5: imidazole / dimethylformamide / 1.5 h / Ambient temperature

6: 80 percent AcOH / tetrahydrofuran / 12 h / Ambient temperature

7: 70 percent / PPh₃, I₂, imidazole / benzene / 30 h / 80 °C

With pyridine; 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; iodine; acetic acid; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jm990050i

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → N4-benzoyl-1-<3-O-(tert-butyldimethylsilyl)-5-O-(tert-butyldiphenylsilyl)-2-deoxy-4α-iodomethyl-β-D-ribo-pentofuranosyl>cytosine (232588-83-9)

Guidance literature:

Multi-step reaction with 8 steps

1: imidazole / dimethylformamide / 15 h / Ambient temperature

2: TFA / CH₂Cl₂ / 2 h / Ambient temperature

3: 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, DMSO / benzene / 0.5 h / Ambient temperature

4: 1.) 2 M NaOH, 2.) NaBH₄ / 1.) 1,4-dioxane, water, RT, 10 min, 2.) EtOH, 0 deg C, 20 min

5: pyridine / 0.83 h / Ambient temperature

6: imidazole / dimethylformamide / 1.5 h / Ambient temperature

7: 80 percent AcOH / tetrahydrofuran / 12 h / Ambient temperature

8: 70 percent / PPh₃, I₂, imidazole / benzene / 30 h / 80 °C

With pyridine; 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; iodine; acetic acid; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jm990050i

upstream raw materials:

N⁴-benzoyl-1-<3-O-(tert-butyldimethylsilyl)-5-O-(tert-butyldiphenylsilyl)-2-deoxy-4α-hydroxymethyl-β-D-ribo-pentofuranosyl>cytosine

N⁴-Benzoyl-5'-O-(dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-2'-deoxycytidine

tert-butyldimethylsilyl chloride

4-N-Benzoyl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)cytidine

Downstream raw materials:

1-<3-O-(tert-butyldimethylsilyl)-5-O-(tert-butyldiphenylsilyl)-2-deoxy-4α-methyl-β-D-ribo-pentofuranosyl>cytosine

N⁴-benzoyl-1-<3-O-(tert-butyldimethylsilyl)-5-O-(tert-butyldiphenylsilyl)-2-deoxy-4α-methyl-β-D-ribo-pentofuranosyl>cytosine

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