(2'S)-β-D-N⁴-benzoyl-5'-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-trifluoromethylcytidine

Base Information

• Chemical Name: (2'S)-β-D-N⁴-benzoyl-5'-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-trifluoromethylcytidine
• CAS No.: 307298-37-9
• Molecular Formula: C₂₃H₃₀F₃N₃O₄Si
• Molecular Weight: 497.59

Synonyms:(2'S)-β-D-N⁴-benzoyl-5'-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-trifluoromethylcytidine

Chemical Property of (2'S)-β-D-N⁴-benzoyl-5'-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-trifluoromethylcytidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (2'S)-β-D-N⁴-benzoyl-5'-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-trifluoromethylcytidine

There total 6 articles about (2'S)-β-D-N⁴-benzoyl-5'-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-trifluoromethylcytidine 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: 54.0%

4-N-benzoylcytosine (26661-13-2) + (2S,4S)-1-O-acetyl-5-(tert-butyldimethylsilyl)-2,3-dideoxy-2-trifluoromethylpentofuranose → (2'S)-α-D-N4-benzoyl-5'-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-trifluoromethylcytidine (307298-39-1) + (2'S)-β-D-N4-benzoyl-5'-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-trifluoromethylcytidine (307298-37-9)

Guidance literature:

4-N-benzoylcytosine; (2S,4S)-1-O-acetyl-5-(tert-butyldimethylsilyl)-2,3-dideoxy-2-trifluoromethylpentofuranose; With N,O-bis-(trimethylsilyl)-acetamide; In acetonitrile; for 0.5h; Heating;

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 20 ℃; for 24h; Further stages.;

DOI:10.1021/jo005520r

Reference yield:

(Z)/(E)-ethyl 3-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-bromo-2-propenoate (182969-96-6) → (2'S)-β-D-N4-benzoyl-5'-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-trifluoromethylcytidine (307298-37-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 68 percent / CuI / dimethylformamide; hexamethylphosphoric acid triamide / 29 h / 75 °C

2.1: H₂ / Pd/C / ethanol / 24 h / 20 °C / 760.05 Torr

2.2: 78 percent / HCl / H₂O / 50 - 55 °C

3.1: 37 percent / imidazole / CH₂Cl₂ / 0.83 h / 20 °C

4.1: 91 percent / DIBAL-H / tetrahydrofuran; cyclohexane / 5 h / -78 °C

5.1: 100 percent / DMAP / CH₂Cl₂ / 20 °C

6.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 0.5 h / Heating

6.2: 54 percent / TMSOTf / acetonitrile / 24 h / 20 °C

With 1H-imidazole; dmap; copper(l) iodide; N,O-bis-(trimethylsilyl)-acetamide; hydrogen; diisobutylaluminium hydride; palladium on activated charcoal; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; cyclohexane; N,N-dimethyl-formamide; acetonitrile; 1.1: Substitution / 2.1: Catalytic hydrogenation / 2.2: Substitution / 3.1: Substitution / 4.1: Reduction / 5.1: Acetylation / 6.1: Condensation / 6.2: Substitution;

DOI:10.1021/jo005520r

Reference yield:

(Z)/(E)-ethyl 3-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-trifluoromethyl-2-propenoate (402757-16-8) → (2'S)-β-D-N4-benzoyl-5'-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-trifluoromethylcytidine (307298-37-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: H₂ / Pd/C / ethanol / 24 h / 20 °C / 760.05 Torr

1.2: 78 percent / HCl / H₂O / 50 - 55 °C

2.1: 37 percent / imidazole / CH₂Cl₂ / 0.83 h / 20 °C

3.1: 91 percent / DIBAL-H / tetrahydrofuran; cyclohexane / 5 h / -78 °C

4.1: 100 percent / DMAP / CH₂Cl₂ / 20 °C

5.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 0.5 h / Heating

5.2: 54 percent / TMSOTf / acetonitrile / 24 h / 20 °C

With 1H-imidazole; dmap; N,O-bis-(trimethylsilyl)-acetamide; hydrogen; diisobutylaluminium hydride; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; cyclohexane; acetonitrile; 1.1: Catalytic hydrogenation / 1.2: Substitution / 2.1: Substitution / 3.1: Reduction / 4.1: Acetylation / 5.1: Condensation / 5.2: Substitution;

DOI:10.1021/jo005520r

upstream raw materials:

4-N-benzoylcytosine

(Z)/(E)-ethyl 3-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-bromo-2-propenoate

(Z)/(E)-ethyl 3-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-trifluoromethyl-2-propenoate

(2R,4S/2S,4S)-5-hydroxy-2-trifluoromethylpentan-4-olide

Downstream raw materials:

N-[1-((2R,3S,5S)-5-Hydroxymethyl-3-trifluoromethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-benzamide

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