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

Base Information

• Chemical Name: N⁴-benzoyl-1-<3-O-(tert-butyldimethylsilyl)-2-deoxy-4α-hydroxymethyl-β-D-ribo-pentofuranosyl>cytosine
• CAS No.: 232588-73-7
• Molecular Formula: C₂₃H₃₃N₃O₆Si
• Molecular Weight: 475.617

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

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

There total 6 articles about N⁴-benzoyl-1-<3-O-(tert-butyldimethylsilyl)-2-deoxy-4α-hydroxymethyl-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:

N4-Benzoyl-5'-O-(dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-2'-deoxycytidine (93134-40-8) → N4-benzoyl-1-<3-O-(tert-butyldimethylsilyl)-2-deoxy-4α-hydroxymethyl-β-D-ribo-pentofuranosyl>cytosine (232588-73-7)

Guidance literature:

Multi-step reaction with 3 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

With sodium hydroxide; sodium tetrahydroborate; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In dichloromethane; benzene;

DOI:10.1021/jm990050i

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → N4-benzoyl-1-<3-O-(tert-butyldimethylsilyl)-2-deoxy-4α-hydroxymethyl-β-D-ribo-pentofuranosyl>cytosine (232588-73-7)

Guidance literature:

Multi-step reaction with 4 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

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

DOI:10.1021/jm990050i

Reference yield:

4-N-Benzoyl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)cytidine (67219-55-0) → N4-benzoyl-1-<3-O-(tert-butyldimethylsilyl)-2-deoxy-4α-hydroxymethyl-β-D-ribo-pentofuranosyl>cytosine (232588-73-7)

Guidance literature:

Multi-step reaction with 4 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

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

DOI:10.1021/jm990050i

upstream raw materials:

formaldehyd

5'-aldehyde-3'-O-tert-butyldimethylsilyl-N-benzoyl-cytidine

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

tert-butyldimethylsilyl chloride

Downstream raw materials:

N-{1-[5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-hydroxymethyl-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide

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

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

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

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