ethyl 1-<2-deoxy-3,5-bis-O-(4-methylbenzoyl)-β-D-ribofuranosyl>-5-methyl-4-nitro-1H-pyrazole-3-carboxylate

Base Information

• Chemical Name: ethyl 1-<2-deoxy-3,5-bis-O-(4-methylbenzoyl)-β-D-ribofuranosyl>-5-methyl-4-nitro-1H-pyrazole-3-carboxylate
• CAS No.: 138836-89-2
• Molecular Formula: C₂₈H₂₉N₃O₉
• Molecular Weight: 551.553
• Mol file: 138836-89-2.mol

Synonyms:ethyl 1-<2-deoxy-3,5-bis-O-(4-methylbenzoyl)-β-D-ribofuranosyl>-5-methyl-4-nitro-1H-pyrazole-3-carboxylate

Chemical Property of ethyl 1-<2-deoxy-3,5-bis-O-(4-methylbenzoyl)-β-D-ribofuranosyl>-5-methyl-4-nitro-1H-pyrazole-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 1-<2-deoxy-3,5-bis-O-(4-methylbenzoyl)-β-D-ribofuranosyl>-5-methyl-4-nitro-1H-pyrazole-3-carboxylate

There total 1 articles about ethyl 1-<2-deoxy-3,5-bis-O-(4-methylbenzoyl)-β-D-ribofuranosyl>-5-methyl-4-nitro-1H-pyrazole-3-carboxylate 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: 46.0%

ethyl 3-methyl-4-nitro-1H-pyrazole-5-carboxylate (28668-07-7) + 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride (4330-21-6) → ethyl 1-<2-deoxy-3,5-bis-O-(4-methylbenzoyl)-β-D-ribofuranosyl>-5-methyl-4-nitro-1H-pyrazole-3-carboxylate (138836-89-2) + ethyl 1-<2-deoxy-3,5-bis-O-(4-methylbenzoyl)-β-D-ribofuranosyl>-3-methyl-4-nitro-1H-pyrazole-5-carboxylate (138836-82-5)

Guidance literature:

With sodium hydride; In acetonitrile; for 1h;

DOI:10.1021/ja00030a050

Reference yield:

ethyl 1-<2-deoxy-3,5-bis-O-(4-methylbenzoyl)-β-D-ribofuranosyl>-5-methyl-4-nitro-1H-pyrazole-3-carboxylate (138836-89-2) → Diisopropyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-isobutyrylamino-3-methyl-7-oxo-6,7-dihydro-pyrazolo[4,3-d]pyrimidin-2-yl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester (138836-94-9,138836-97-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 85 percent / NH₃, CH₃OH / 24 h / 120 °C

2: H₂ / 10percent Pd/C / ethanol; H₂O / 5 h / 2585.7 Torr / Ambient temperature

3: 80 percent / pyridine / 0.75 h / Heating

4: 1.) conc. NH₄OH, 30percent aq. H₂O₂, 2.) NH₃ / 1.) 0 deg C, 40 min, 2.) 120 deg C, 12 h

5: 1.) Me₃SiCl, pyridine / 1.) 0 deg C, 30 min, 2.) RT, 3 h

6: 75 percent / pyridine / 4 °C

7: 82 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 1 h

With pyridine; methanol; ammonium hydroxide; chloro-trimethyl-silane; ammonia; hydrogen; dihydrogen peroxide; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In pyridine; ethanol; dichloromethane; water;

DOI:10.1021/ja00030a050

Reference yield:

ethyl 1-<2-deoxy-3,5-bis-O-(4-methylbenzoyl)-β-D-ribofuranosyl>-5-methyl-4-nitro-1H-pyrazole-3-carboxylate (138836-89-2) → N-<2-<5-O--2-deoxy-β-D-ribofuranosyl>-3-methyl-7-oxo-2H-pyrazolo<4,3-d>pyrimidin-5-yl>-2-methylpropanamide (138856-94-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 85 percent / NH₃, CH₃OH / 24 h / 120 °C

2: H₂ / 10percent Pd/C / ethanol; H₂O / 5 h / 2585.7 Torr / Ambient temperature

3: 80 percent / pyridine / 0.75 h / Heating

4: 1.) conc. NH₄OH, 30percent aq. H₂O₂, 2.) NH₃ / 1.) 0 deg C, 40 min, 2.) 120 deg C, 12 h

5: 1.) Me₃SiCl, pyridine / 1.) 0 deg C, 30 min, 2.) RT, 3 h

6: 75 percent / pyridine / 4 °C

With pyridine; methanol; ammonium hydroxide; chloro-trimethyl-silane; ammonia; hydrogen; dihydrogen peroxide; palladium on activated charcoal; In pyridine; ethanol; water;

DOI:10.1021/ja00030a050

upstream raw materials:

ethyl 3-methyl-4-nitro-1H-pyrazole-5-carboxylate

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride

Downstream raw materials:

N-<2-<5-O--2-deoxy-β-D-ribofuranosyl>-3-methyl-7-oxo-2H-pyrazolo<4,3-d>pyrimidin-5-yl>-2-methylpropanamide

Diisopropyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-isobutyrylamino-3-methyl-7-oxo-6,7-dihydro-pyrazolo[4,3-d]pyrimidin-2-yl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester