N⁴-benzoyl-1-[5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2,3-didehydro-2-fluoro-4-thio-β-D-ribofuranosyl]-5-fluorocytosine

Base Information

• Chemical Name: N⁴-benzoyl-1-[5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2,3-didehydro-2-fluoro-4-thio-β-D-ribofuranosyl]-5-fluorocytosine
• CAS No.: 476210-06-7
• Molecular Formula: C₃₂H₃₁F₂N₃O₃SSi
• Molecular Weight: 603.765

Synonyms:N⁴-benzoyl-1-[5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2,3-didehydro-2-fluoro-4-thio-β-D-ribofuranosyl]-5-fluorocytosine

Chemical Property of N⁴-benzoyl-1-[5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2,3-didehydro-2-fluoro-4-thio-β-D-ribofuranosyl]-5-fluorocytosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N⁴-benzoyl-1-[5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2,3-didehydro-2-fluoro-4-thio-β-D-ribofuranosyl]-5-fluorocytosine

There total 13 articles about N⁴-benzoyl-1-[5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2,3-didehydro-2-fluoro-4-thio-β-D-ribofuranosyl]-5-fluorocytosine 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: 69.0%

N4-benzoyl-1-[(1R,2R,4S)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselanyl-4-thio-β-D-pentofuranosyl]-5-fluorocytosine (476209-98-0) → N4-benzoyl-1-[5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2,3-didehydro-2-fluoro-4-thio-β-D-ribofuranosyl]-5-fluorocytosine (476210-06-7)

Guidance literature:

N⁴-benzoyl-1-[(1R,2R,4S)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselanyl-4-thio-β-D-pentofuranosyl]-5-fluorocytosine; With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -78 ℃;

With pyridine; In dichloromethane; at 20 ℃; Further stages.;

DOI:10.1021/jm020246+

Reference yield:

5-(tert-butyl-diphenyl-silanyloxymethyl)-3-fluoro-5H-furan-2-one → N4-benzoyl-1-[5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2,3-didehydro-2-fluoro-4-thio-β-D-ribofuranosyl]-5-fluorocytosine (476210-06-7)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 94 percent / H₂ / 5 percent Pd/C / ethyl acetate / 3 h

2.1: NaOH / ethanol; H₂O / 2 h / 20 °C

2.2: dimethylsulfoxide / 1 h

3.1: 7.52 g / I₂; imidazole; PPh₃ / toluene / 4 h / 60 °C

4.1: 87 percent / dimethylformamide / 8 h / 20 °C

5.1: DIBAL-H / toluene; hexane / 1 h / -78 °C

6.1: Ac₂O; DMSO / 24 h / 20 °C

7.1: LiHMDS / tetrahydrofuran / 1 h / -78 °C

7.2: TMSCl / tetrahydrofuran / -78 - 20 °C

7.3: 72 percent / tetrahydrofuran / 1 h / -78 °C

8.1: DIBAL-H / hexane; toluene / 1 h / -78 °C

9.1: TEA; DMAP / CH₂Cl₂ / 3 h / 20 °C

10.1: TMSOTf / acetonitrile

11.1: mCPBA / CH₂Cl₂ / -78 °C

11.2: 69 percent / pyridine / CH₂Cl₂ / 20 °C

With 1H-imidazole; dmap; sodium hydroxide; trimethylsilyl trifluoromethanesulfonate; TEA; hydrogen; iodine; acetic anhydride; diisobutylaluminium hydride; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium hexamethyldisilazane; 5 percent Pd/C; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; 6.1: Moffat-type oxidation;

DOI:10.1021/jm020246+

Reference yield:

N-benzoyl-5-fluorocytosine (10357-07-0) → N4-benzoyl-1-[5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2,3-didehydro-2-fluoro-4-thio-β-D-ribofuranosyl]-5-fluorocytosine (476210-06-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: acetonitrile / Heating

2.1: TMSOTf / acetonitrile

3.1: mCPBA / CH₂Cl₂ / -78 °C

3.2: 69 percent / pyridine / CH₂Cl₂ / 20 °C

With trimethylsilyl trifluoromethanesulfonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; acetonitrile;

DOI:10.1021/jm020246+

upstream raw materials:

N⁴-benzoyl-1-[(1R,2R,4S)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselanyl-4-thio-β-D-pentofuranosyl]-5-fluorocytosine

N-benzoyl-5-fluorocytosine

(2S,4S)-(+)-4-tert-butyldiphenylsilyloxymethyl-2-fluoro-γ-butyrolactone

(3S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-fluoro-dihydro-thiophen-2-one

Downstream raw materials:

N-[5-Fluoro-1-((2R,5S)-3-fluoro-5-hydroxymethyl-2,5-dihydro-thiophen-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-benzamide

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