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

Base Information

• Chemical Name: 1-<3-O-(tert-butyldimethylsilyl)-5-O-(tert-butyldiphenylsilyl)-2-deoxy-4α-methyl-β-D-ribo-pentofuranosyl>cytosine
• CAS No.: 232588-87-3
• Molecular Formula: C₃₂H₄₇N₃O₄Si₂
• Molecular Weight: 593.914

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 12 articles about 1-<3-O-(tert-butyldimethylsilyl)-5-O-(tert-butyldiphenylsilyl)-2-deoxy-4α-methyl-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: 98.0%

N4-benzoyl-1-<3-O-(tert-butyldimethylsilyl)-5-O-(tert-butyldiphenylsilyl)-2-deoxy-4α-methyl-β-D-ribo-pentofuranosyl>cytosine (232588-84-0) → 1-<3-O-(tert-butyldimethylsilyl)-5-O-(tert-butyldiphenylsilyl)-2-deoxy-4α-methyl-β-D-ribo-pentofuranosyl>cytosine (232588-87-3)

Guidance literature:

With methanol; 1,8-diazabicyclo[5.4.0]undec-7-ene; for 0.5h; Ambient temperature;

DOI:10.1021/jm990050i

Reference yield:

N4-Benzoyl-5'-O-(dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-2'-deoxycytidine (93134-40-8) → 1-<3-O-(tert-butyldimethylsilyl)-5-O-(tert-butyldiphenylsilyl)-2-deoxy-4α-methyl-β-D-ribo-pentofuranosyl>cytosine (232588-87-3)

Guidance literature:

Multi-step reaction with 9 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

8: 77 percent / Et₃N, H₂ / 10 percent Pd/C / ethanol; ethyl acetate / 2 h / Ambient temperature

9: 98 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene, methanol / 0.5 h / Ambient temperature

With pyridine; 1H-imidazole; methanol; sodium hydroxide; sodium tetrahydroborate; hydrogen; iodine; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jm990050i

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 1-<3-O-(tert-butyldimethylsilyl)-5-O-(tert-butyldiphenylsilyl)-2-deoxy-4α-methyl-β-D-ribo-pentofuranosyl>cytosine (232588-87-3)

Guidance literature:

Multi-step reaction with 10 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

9: 77 percent / Et₃N, H₂ / 10 percent Pd/C / ethanol; ethyl acetate / 2 h / Ambient temperature

10: 98 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene, methanol / 0.5 h / Ambient temperature

With pyridine; 1H-imidazole; methanol; sodium hydroxide; sodium tetrahydroborate; hydrogen; iodine; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; 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-methyl-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

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