methyl 5-O-benzyl-2-O-benzoyl-3-fluoro-3-deoxy-β-D-ribofuranoside

Base Information

• Chemical Name: methyl 5-O-benzyl-2-O-benzoyl-3-fluoro-3-deoxy-β-D-ribofuranoside
• CAS No.: 124939-88-4
• Molecular Formula: C₂₀H₂₁FO₅
• Molecular Weight: 360.382
• Mol file: 124939-88-4.mol

Synonyms:methyl 5-O-benzyl-2-O-benzoyl-3-fluoro-3-deoxy-β-D-ribofuranoside

Chemical Property of methyl 5-O-benzyl-2-O-benzoyl-3-fluoro-3-deoxy-β-D-ribofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 5-O-benzyl-2-O-benzoyl-3-fluoro-3-deoxy-β-D-ribofuranoside

There total 5 articles about methyl 5-O-benzyl-2-O-benzoyl-3-fluoro-3-deoxy-β-D-ribofuranoside 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: 39.8%

Potassium benzoate (582-25-2) + methyl 5-O-benzyl-2-O-tosyl-3-fluoro-3-deoxy-β-D-arabino-furanoside (126716-24-3) → methyl 5-O-benzyl-3-fluoro-3-deoxy-β-D-ribofuranoside (133776-28-0) + methyl 5-O-benzyl-2-O-benzoyl-3-fluoro-3-deoxy-β-D-ribofuranoside (124939-88-4)

Guidance literature:

With dibenzo-18-crown-6; In dimethyl sulfoxide; at 205 - 210 ℃; for 4h;

DOI:10.1021/jm00111a040

Reference yield:

methyl 5-O-benzyl-3-fluoro-3-deoxy-β-D-arabino-furanoside (28867-47-2) → methyl 5-O-benzyl-2-O-benzoyl-3-fluoro-3-deoxy-β-D-ribofuranoside (124939-88-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / pyridine / 28 h / Ambient temperature

2: 39.8 percent / dibenzo-18-crown-6 / dimethylsulfoxide / 4 h / 205 - 210 °C

With pyridine; dibenzo-18-crown-6; In dimethyl sulfoxide;

DOI:10.1021/jm00111a040

Reference yield:

methyl 5-O-benzyl-2,3-anhydro-β-D-lyxofuranoside (29024-87-1) → methyl 5-O-benzyl-2-O-benzoyl-3-fluoro-3-deoxy-β-D-ribofuranoside (124939-88-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 31 percent / KHF₂, NaF / ethane-1,2-diol / 4 h / Heating

2: 89 percent / pyridine / 28 h / Ambient temperature

3: 39.8 percent / dibenzo-18-crown-6 / dimethylsulfoxide / 4 h / 205 - 210 °C

With pyridine; dibenzo-18-crown-6; potassium hydrogen bifluoride; sodium fluoride; In ethylene glycol; dimethyl sulfoxide;

DOI:10.1021/jm00111a040

upstream raw materials:

Potassium benzoate

methyl 5-O-benzyl-2-O-tosyl-3-fluoro-3-deoxy-β-D-arabino-furanoside

methyl 5-O-benzyl-3-fluoro-3-deoxy-β-D-arabino-furanoside

methyl 5-O-benzyl-2,3-anhydro-β-D-lyxofuranoside

Downstream raw materials:

(2R,3S,4S,5R)-2-(6-amino-9H-purine-9-yl)-4-fluoro-5-(hydroxymethyl)tetrahydrofuran-3-ol

3'-deoxy-3'-fluorocytidine

2-amino-9-((2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1,9-dihydro-6H-purine-6-one

C₂₃H₂₀FN₃O₆