5-O-Benzoyl-2-deoxy-2-fluoro-1-O-methyl-3-O-(methylthio)thiocarbonyl-β-D-arabinofuranose

Base Information

• Chemical Name: 5-O-Benzoyl-2-deoxy-2-fluoro-1-O-methyl-3-O-(methylthio)thiocarbonyl-β-D-arabinofuranose
• CAS No.: 136228-14-3
• Molecular Formula: C₁₅H₁₇FO₅S₂
• Molecular Weight: 360.427
• Mol file: 136228-14-3.mol

Synonyms:5-O-Benzoyl-2-deoxy-2-fluoro-1-O-methyl-3-O-(methylthio)thiocarbonyl-β-D-arabinofuranose

Chemical Property of 5-O-Benzoyl-2-deoxy-2-fluoro-1-O-methyl-3-O-(methylthio)thiocarbonyl-β-D-arabinofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-O-Benzoyl-2-deoxy-2-fluoro-1-O-methyl-3-O-(methylthio)thiocarbonyl-β-D-arabinofuranose

There total 4 articles about 5-O-Benzoyl-2-deoxy-2-fluoro-1-O-methyl-3-O-(methylthio)thiocarbonyl-β-D-arabinofuranose 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:

2-deoxy-2-fluoro-3,5-di-O-benzoyl-α-D-arabinofuranosyl bromide (97614-44-3) → 5-O-Benzoyl-2-deoxy-2-fluoro-1-O-methyl-3-O-(methylthio)thiocarbonyl-β-D-arabinofuranose (136228-14-3)

Guidance literature:

Multi-step reaction with 4 steps

1: K₂CO₃ / tetrahydrofuran / Ambient temperature

2: 78 percent / pyridine / -30 °C

3: NaH / dimethylformamide / 0 °C

4: 0 °C

With pyridine; sodium hydride; potassium carbonate; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jm00090a008

Reference yield:

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose (97614-43-2) → 5-O-Benzoyl-2-deoxy-2-fluoro-1-O-methyl-3-O-(methylthio)thiocarbonyl-β-D-arabinofuranose (136228-14-3)

Guidance literature:

Multi-step reaction with 5 steps

1: HBr, AcOH / CH₂Cl₂ / Ambient temperature

2: K₂CO₃ / tetrahydrofuran / Ambient temperature

3: 78 percent / pyridine / -30 °C

4: NaH / dimethylformamide / 0 °C

5: 0 °C

With pyridine; hydrogen bromide; sodium hydride; potassium carbonate; acetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00090a008

Reference yield:

2-Deoxy-2-fluoro-1-O-methyl-β-D-arabinofuranose (136315-44-1) → 5-O-Benzoyl-2-deoxy-2-fluoro-1-O-methyl-3-O-(methylthio)thiocarbonyl-β-D-arabinofuranose (136228-14-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 78 percent / pyridine / -30 °C

2: NaH / dimethylformamide / 0 °C

3: 0 °C

With pyridine; sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1021/jm00090a008

upstream raw materials:

2-deoxy-2-fluoro-3,5-di-O-benzoyl-α-D-arabinofuranosyl bromide

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose

2-Deoxy-2-fluoro-1-O-methyl-β-D-arabinofuranose

5-O-Benzoyl-2-deoxy-2-fluoro-1-O-methyl-β-D-arabinofuranose

Downstream raw materials:

5-O-Benzoyl-2,3-dideoxy-2-fluoro-1-O-methyl-β-D-threo-pentofuranose

iodenosine

1-(5-O-benzoyl-2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)cytosine

1-(2,3-Dideoxy-2-fluoro-β-D-arabinofuranosyl)-cytosine

Refernces

• 1、 Wysocki Jr.,Siddiqui,Barchi Jr.,Driscoll,Marquez. "A more expedient approach to the synthesis of anti-HIV-active 2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl nucleosides". . p. 1005 - 1008. Retrieved 2007/10/02.