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

Base Information

• Chemical Name: (2'R)-β-D-N⁴-benzoyl-5'-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-trifluoromethylcytidine
• CAS No.: 307298-24-4
• Molecular Formula: C₂₃H₃₀F₃N₃O₄Si
• Molecular Weight: 497.59

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about (2'R)-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: 53.0%

4-N-benzoylcytosine (26661-13-2) + (2R,4S)-1-O-acetyl-5-(tert-butyldimethylsilyl)-2,3-dideoxy-2-trifluoromethylpentofuranose (307298-21-1) → (2'R)-α-D-N4-benzoyl-5'-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-trifluoromethylcytidine (307298-27-7) + (2'R)-β-D-N4-benzoyl-5'-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-trifluoromethylcytidine (307298-24-4)

Guidance literature:

4-N-benzoylcytosine; (2R,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'R)-β-D-N4-benzoyl-5'-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-trifluoromethylcytidine (307298-24-4)

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: 53 percent / imidazole / CH₂Cl₂ / 0.83 h / 20 °C

4.1: 64 percent / DIBAL-H / tetrahydrofuran; cyclohexane / 5 h / -78 °C

5.1: 93 percent / DMAP / CH₂Cl₂ / 20 °C

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

6.2: 53 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'R)-β-D-N4-benzoyl-5'-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-trifluoromethylcytidine (307298-24-4)

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: 53 percent / imidazole / CH₂Cl₂ / 0.83 h / 20 °C

3.1: 64 percent / DIBAL-H / tetrahydrofuran; cyclohexane / 5 h / -78 °C

4.1: 93 percent / DMAP / CH₂Cl₂ / 20 °C

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

5.2: 53 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

(2R,4S)-1-O-acetyl-5-(tert-butyldimethylsilyl)-2,3-dideoxy-2-trifluoromethylpentofuranose

(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

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 307298-24-4 (2'R)-β-D-N⁴-benzoyl-5'-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-trifluoromethylcytidine

Send

Send

Metric Ton KG G Pound L ML

Send

Send