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

Base Information

• Chemical Name: (-)-N⁴-benzoyl-1-[(1S,2S,4R)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselenyl-4-thio-β-L-ribofuranosyl]-5-fluorocytosine
• CAS No.: 479035-92-2
• Molecular Formula: C₃₈H₃₇F₂N₃O₃SSeSi
• Molecular Weight: 760.838
• Mol file: 479035-92-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about (-)-N⁴-benzoyl-1-[(1S,2S,4R)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselenyl-4-thio-β-L-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: 59.0%

N-benzoyl-5-fluorocytosine (10357-07-0) + (1S/R,2S,4R)-1-O-aceyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselenyl-4-thio-β-L-ribofuranoside (398133-34-1) → (-)-N4-benzoyl-1-[(1S,2S,4R)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselenyl-4-thio-β-L-ribofuranosyl]-5-fluorocytosine (479035-92-2)

Guidance literature:

N-benzoyl-5-fluorocytosine; With 1,1,1,3,3,3-hexamethyl-disilazane; In acetonitrile; for 5h; Heating;

(1S/R,2S,4R)-1-O-aceyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselenyl-4-thio-β-L-ribofuranoside; With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 20 ℃; for 16h; Further stages.;

DOI:10.1021/jm020376i

Reference yield:

Phenylselenyl bromide (34837-55-3) → (-)-N4-benzoyl-1-[(1S,2S,4R)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselenyl-4-thio-β-L-ribofuranosyl]-5-fluorocytosine (479035-92-2)

Guidance literature:

Multi-step reaction with 4 steps

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

1.2: TMSCl / tetrahydrofuran / 20 °C

1.3: 74 percent / tetrahydrofuran / 1 h / -78 °C

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

3.1: TEA; 4-DMAP / CH₂Cl₂ / 3 h / 20 °C

4.1: HMDS / acetonitrile / 5 h / Heating

4.2: 59 percent / TMSOTf / acetonitrile / 16 h / 20 °C

With dmap; TEA; diisobutylaluminium hydride; 1,1,1,3,3,3-hexamethyl-disilazane; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane; toluene; acetonitrile;

DOI:10.1021/jm020376i

Reference yield:

(2R,4R)-(-)-4-tert-butyldiphenylsilyloxymethyl-2-fluoro-γ-butyrolactone (398133-29-4) → (-)-N4-benzoyl-1-[(1S,2S,4R)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselenyl-4-thio-β-L-ribofuranosyl]-5-fluorocytosine (479035-92-2)

Guidance literature:

Multi-step reaction with 10 steps

1.1: aq. NaOH / ethanol / 2 h / 20 °C

2.1: dimethylsulfoxide / 1 h

3.1: 82 percent / I₂; Ph₃P; imidazole / toluene / 4 h / 60 °C

4.1: 91 percent / dimethylformamide / 8 h / 20 °C

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

6.1: Ac₂O; DMSO / 24 h / 20 °C

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

7.2: TMSCl / tetrahydrofuran / 20 °C

7.3: 74 percent / tetrahydrofuran / 1 h / -78 °C

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

9.1: TEA; 4-DMAP / CH₂Cl₂ / 3 h / 20 °C

10.1: HMDS / acetonitrile / 5 h / Heating

10.2: 59 percent / TMSOTf / acetonitrile / 16 h / 20 °C

With 1H-imidazole; dmap; sodium hydroxide; TEA; iodine; acetic anhydride; diisobutylaluminium hydride; dimethyl sulfoxide; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; 3.1: Mitsunobu reaction / 6.1: Moffatt-type oxidation;

DOI:10.1021/jm020376i

upstream raw materials:

N-benzoyl-5-fluorocytosine

(1S/R,2S,4R)-1-O-aceyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselenyl-4-thio-β-L-ribofuranoside

Phenylselenyl bromide

(2R,4R)-(-)-4-tert-butyldiphenylsilyloxymethyl-2-fluoro-γ-butyrolactone

Downstream raw materials:

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

Refernces