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

Base Information

• Chemical Name: (+)-N⁴-benzoyl-1-[(1R,2R,4S)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselenyl-4-thio-β-D-ribofuranosyl]-5-fluorocytosine
• CAS No.: 476209-96-8
• Molecular Formula: C₃₈H₃₈FN₃O₃SSeSi
• Molecular Weight: 742.848

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (+)-N⁴-benzoyl-1-[(1R,2R,4S)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselenyl-4-thio-β-D-ribofuranosyl]-5-fluorocytosine

There total 11 articles about (+)-N⁴-benzoyl-1-[(1R,2R,4S)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselenyl-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:

4-N-benzoylcytosine (26661-13-2) → (+)-N4-benzoyl-1-[(1R,2R,4S)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselenyl-4-thio-β-D-ribofuranosyl]-5-fluorocytosine (476209-96-8)

Guidance literature:

Multi-step reaction with 2 steps

1: acetonitrile / 5 h / Heating

2: 0.269 g / TMSOTf / acetonitrile / 16 h

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile;

DOI:10.1021/jm020246+

Reference yield:

Phenylselenyl bromide (34837-55-3) → (+)-N4-benzoyl-1-[(1R,2R,4S)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselenyl-4-thio-β-D-ribofuranosyl]-5-fluorocytosine (476209-96-8)

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: 0.269 g / TMSOTf / acetonitrile / 16 h

With dmap; trimethylsilyl trifluoromethanesulfonate; TEA; diisobutylaluminium hydride; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane; toluene; 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-phenylselenyl-4-thio-β-D-ribofuranosyl]-5-fluorocytosine (476209-96-8)

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: 0.269 g / TMSOTf / acetonitrile / 16 h

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:

N-(2-((1-trimethylsilyl)oxy)pyrimidin-4-yl)benzamide

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

4-N-benzoylcytosine

Phenylselenyl bromide

Downstream raw materials:

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

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