Benzoic acid (2R,3S,4S,5R)-5-(2-acetylamino-6-oxo-1,6-dihydro-purin-9-yl)-4-azido-3-fluoro-tetrahydro-furan-2-ylmethyl ester

Base Information

• Chemical Name: Benzoic acid (2R,3S,4S,5R)-5-(2-acetylamino-6-oxo-1,6-dihydro-purin-9-yl)-4-azido-3-fluoro-tetrahydro-furan-2-ylmethyl ester
• CAS No.: 133776-33-7
• Molecular Formula: C₁₉H₁₇FN₈O₅
• Molecular Weight: 456.393
• Mol file: 133776-33-7.mol

Synonyms:Benzoic acid (2R,3S,4S,5R)-5-(2-acetylamino-6-oxo-1,6-dihydro-purin-9-yl)-4-azido-3-fluoro-tetrahydro-furan-2-ylmethyl ester

Chemical Property of Benzoic acid (2R,3S,4S,5R)-5-(2-acetylamino-6-oxo-1,6-dihydro-purin-9-yl)-4-azido-3-fluoro-tetrahydro-furan-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2R,3S,4S,5R)-5-(2-acetylamino-6-oxo-1,6-dihydro-purin-9-yl)-4-azido-3-fluoro-tetrahydro-furan-2-ylmethyl ester

There total 11 articles about Benzoic acid (2R,3S,4S,5R)-5-(2-acetylamino-6-oxo-1,6-dihydro-purin-9-yl)-4-azido-3-fluoro-tetrahydro-furan-2-ylmethyl ester 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: 22.0%

bis(trimethylsilyl)-N2-acetylguanine (107937-54-2) + 2-azido-5-O-benzoyl-3-fluoro-2,3-dideoxy-β-D-ribofuranoside (133776-29-1) → Benzoic acid (2R,3S,4S,5R)-5-(2-acetylamino-6-oxo-1,6-dihydro-purin-9-yl)-4-azido-3-fluoro-tetrahydro-furan-2-ylmethyl ester (133776-33-7) + Benzoic acid (2R,3S,4S,5S)-5-(2-acetylamino-6-oxo-1,6-dihydro-purin-9-yl)-4-azido-3-fluoro-tetrahydro-furan-2-ylmethyl ester (133776-21-3) + Benzoic acid (2R,3S,4S,5R)-5-(2-acetylamino-6-oxo-1,6-dihydro-purin-7-yl)-4-azido-3-fluoro-tetrahydro-furan-2-ylmethyl ester (133776-34-8) + Benzoic acid (2R,3S,4S,5S)-5-(2-acetylamino-6-oxo-1,6-dihydro-purin-7-yl)-4-azido-3-fluoro-tetrahydro-furan-2-ylmethyl ester (133776-22-4)

Guidance literature:

With trimethyl((trifluoromethyl)sulfonyl)silane; In acetonitrile; for 3h; Title compound not separated from byproducts; Heating;

DOI:10.1021/jm00111a040

Reference yield:

methyl 5-O-benzyl-3-fluoro-3-deoxy-β-D-arabino-furanoside (28867-47-2) → Benzoic acid (2R,3S,4S,5R)-5-(2-acetylamino-6-oxo-1,6-dihydro-purin-9-yl)-4-azido-3-fluoro-tetrahydro-furan-2-ylmethyl ester (133776-33-7)

Guidance literature:

Multi-step reaction with 6 steps

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

2: 88 percent / H₂ / 10percent Pd/C / ethanol / 72 h / Ambient temperature

3: 81 percent / pyridine / 12 h / Ambient temperature

4: NaN₃ / dimethylsulfoxide / 1 h / 180 °C

5: pyridine / 12 h / Ambient temperature

6: TMS-Tfl / acetonitrile / 3 h / Heating

With pyridine; sodium azide; hydrogen; trimethyl((trifluoromethyl)sulfonyl)silane; palladium on activated charcoal; In ethanol; dimethyl sulfoxide; acetonitrile;

DOI:10.1021/jm00111a040

Reference yield:

methyl 5-O-benzyl-2,3-anhydro-β-D-lyxofuranoside (29024-87-1) → Benzoic acid (2R,3S,4S,5R)-5-(2-acetylamino-6-oxo-1,6-dihydro-purin-9-yl)-4-azido-3-fluoro-tetrahydro-furan-2-ylmethyl ester (133776-33-7)

Guidance literature:

Multi-step reaction with 7 steps

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

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

3: 88 percent / H₂ / 10percent Pd/C / ethanol / 72 h / Ambient temperature

4: 81 percent / pyridine / 12 h / Ambient temperature

5: NaN₃ / dimethylsulfoxide / 1 h / 180 °C

6: pyridine / 12 h / Ambient temperature

7: TMS-Tfl / acetonitrile / 3 h / Heating

With pyridine; sodium azide; potassium hydrogen bifluoride; hydrogen; trimethyl((trifluoromethyl)sulfonyl)silane; sodium fluoride; palladium on activated charcoal; In ethanol; ethylene glycol; dimethyl sulfoxide; acetonitrile;

DOI:10.1021/jm00111a040

upstream raw materials:

bis(trimethylsilyl)-N²-acetylguanine

2-azido-5-O-benzoyl-3-fluoro-2,3-dideoxy-β-D-ribofuranoside

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

((2R,3S,4S,5R)-4-Azido-3-fluoro-5-methoxy-tetrahydro-furan-2-yl)-methanol