α-2'-Deoxy-2'-difluoromethyl-3',5'-di-O-benzyluridine

Base Information

• Chemical Name: α-2'-Deoxy-2'-difluoromethyl-3',5'-di-O-benzyluridine
• CAS No.: 349654-66-6
• Molecular Formula: C₂₄H₂₄F₂N₂O₅
• Molecular Weight: 458.462
• Mol file: 349654-66-6.mol

Synonyms:α-2'-Deoxy-2'-difluoromethyl-3',5'-di-O-benzyluridine

Chemical Property of α-2'-Deoxy-2'-difluoromethyl-3',5'-di-O-benzyluridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of α-2'-Deoxy-2'-difluoromethyl-3',5'-di-O-benzyluridine

There total 8 articles about α-2'-Deoxy-2'-difluoromethyl-3',5'-di-O-benzyluridine 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: 67.0%

1'-O-Acetyl-2'-deoxy-2'-difluoromethyl-3',5'-di-O-benzyl-α-D-arabinose (349654-65-5) + O,O'-bis-(trimethylsilyl)uracil (10457-14-4) → α-2'-Deoxy-2'-difluoromethyl-3',5'-di-O-benzyluridine (349654-66-6)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In acetonitrile; at 20 ℃; for 24h;

DOI:10.1055/s-2001-13419

Reference yield:

benzyl bromide (100-39-0) → α-2'-Deoxy-2'-difluoromethyl-3',5'-di-O-benzyluridine (349654-66-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 80 percent / NaOH; K₂CO₃ / dimethylsulfoxide

2: 310 mg / Et₃N; DMAP / CH₂Cl₂

3: 85 percent / tributyltin hydride; AIBN / toluene / 2 h / 70 °C

4: HCl / CH₂Cl₂ / 0.17 h

5: 26 mg / 4 Angstroem molecular sieves / CH₂Cl₂ / 48 h

With hydrogenchloride; dmap; sodium hydroxide; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; tri-n-butyl-tin hydride; potassium carbonate; triethylamine; In dichloromethane; dimethyl sulfoxide; toluene;

DOI:10.1055/s-2001-13419

Reference yield:

1,4-anhydro-2-deoxy-3,5-bis-O-(trimethylsilyl)-D-erythro-pent-1-enitol (153975-93-0) → α-2'-Deoxy-2'-difluoromethyl-3',5'-di-O-benzyluridine (349654-66-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 80 percent / NaOH; K₂CO₃ / dimethylsulfoxide

2: 310 mg / Et₃N; DMAP / CH₂Cl₂

3: 85 percent / tributyltin hydride; AIBN / toluene / 2 h / 70 °C

4: HCl / CH₂Cl₂ / 0.17 h

5: 26 mg / 4 Angstroem molecular sieves / CH₂Cl₂ / 48 h

With hydrogenchloride; dmap; sodium hydroxide; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; tri-n-butyl-tin hydride; potassium carbonate; triethylamine; In dichloromethane; dimethyl sulfoxide; toluene;

DOI:10.1055/s-2001-13419

upstream raw materials:

O,O'-bis-(trimethylsilyl)uracil

1'-O-Acetyl-2'-deoxy-2'-difluoromethyl-3',5'-di-O-benzyl-α-D-arabinose

benzyl bromide

1,4-anhydro-2-deoxy-3,5-bis-O-(trimethylsilyl)-D-erythro-pent-1-enitol