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

Base Information

• Chemical Name: N⁴-benzoyl-1-[(1R,2R,4S)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselanyl-4-thio-β-D-pentofuranosyl]-5-fluorocytosine
• CAS No.: 476209-98-0
• Molecular Formula: C₃₈H₃₇F₂N₃O₃SSeSi
• Molecular Weight: 760.838

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about N⁴-benzoyl-1-[(1R,2R,4S)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselanyl-4-thio-β-D-pentofuranosyl]-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:

Phenylselenyl bromide (34837-55-3) → 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)

Guidance literature:

Multi-step reaction with 4 steps

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

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

1.3: 72 percent / tetrahydrofuran / 1 h / -78 °C

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

3.1: TEA; DMAP / CH₂Cl₂ / 3 h / 20 °C

4.1: TMSOTf / acetonitrile

With dmap; trimethylsilyl trifluoromethanesulfonate; TEA; diisobutylaluminium hydride; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane; toluene; acetonitrile;

DOI:10.1021/jm020246+

Reference yield:

N-benzoyl-5-fluorocytosine (10357-07-0) → 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)

Guidance literature:

Multi-step reaction with 2 steps

1: acetonitrile / Heating

2: TMSOTf / acetonitrile

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile;

DOI:10.1021/jm020246+

Reference yield:

(2S,4S)-(+)-4-tert-butyldiphenylsilyloxymethyl-2-fluoro-γ-butyrolactone (476209-84-4) → 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)

Guidance literature:

Multi-step reaction with 9 steps

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

1.2: dimethylsulfoxide / 1 h

2.1: 7.52 g / I₂; imidazole; PPh₃ / toluene / 4 h / 60 °C

3.1: 87 percent / dimethylformamide / 8 h / 20 °C

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

5.1: Ac₂O; DMSO / 24 h / 20 °C

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

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

6.3: 72 percent / tetrahydrofuran / 1 h / -78 °C

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

8.1: TEA; DMAP / CH₂Cl₂ / 3 h / 20 °C

9.1: TMSOTf / acetonitrile

With 1H-imidazole; dmap; sodium hydroxide; trimethylsilyl trifluoromethanesulfonate; TEA; iodine; acetic anhydride; diisobutylaluminium hydride; dimethyl sulfoxide; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 5.1: Moffat-type oxidation;

DOI:10.1021/jm020246+

upstream raw materials:

Acetic acid (3R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-3-fluoro-3-phenylselanyl-tetrahydro-thiophen-2-yl ester

Phenylselenyl bromide

N-benzoyl-5-fluorocytosine

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

Downstream raw materials:

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

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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