Methyl 3-(2,3,5-Tri-O-benzyl-β-D-arabinofuranosyl)-5-cyanopyrazole-4-carboxylate

Base Information

• Chemical Name: Methyl 3-(2,3,5-Tri-O-benzyl-β-D-arabinofuranosyl)-5-cyanopyrazole-4-carboxylate
• CAS No.: 88287-70-1
• Molecular Formula: C₃₂H₃₁N₃O₆
• Molecular Weight: 553.615
• Mol file: 88287-70-1.mol

Synonyms:Methyl 3-(2,3,5-Tri-O-benzyl-β-D-arabinofuranosyl)-5-cyanopyrazole-4-carboxylate

Chemical Property of Methyl 3-(2,3,5-Tri-O-benzyl-β-D-arabinofuranosyl)-5-cyanopyrazole-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl 3-(2,3,5-Tri-O-benzyl-β-D-arabinofuranosyl)-5-cyanopyrazole-4-carboxylate

There total 1 articles about Methyl 3-(2,3,5-Tri-O-benzyl-β-D-arabinofuranosyl)-5-cyanopyrazole-4-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: 54.0%

Methyl 3-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-5-carbamoylpyrazole-4-carboxylate (52646-33-0) → Methyl 3-(2,3,5-Tri-O-benzyl-β-D-arabinofuranosyl)-5-cyanopyrazole-4-carboxylate (88287-70-1)

Guidance literature:

With pyridine; trifluoroacetic anhydride; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1021/jo00177a028

Reference yield: 71.0%

Methyl 3-(2,3,5-Tri-O-benzyl-β-D-arabinofuranosyl)-5-cyanopyrazole-4-carboxylate (88287-70-1) → 3-(2,3,5-Tri-O-benzyl-β-D-arabinofuranosyl)-5-cyanopyrazole-4-carboxylic acid (88287-73-4)

Guidance literature:

With sodium hydroxide; In methanol; water; Heating;

DOI:10.1021/jo00177a028

Reference yield:

Methyl 3-(2,3,5-Tri-O-benzyl-β-D-arabinofuranosyl)-5-cyanopyrazole-4-carboxylate (88287-70-1) → 3-(2,3,5-Tri-O-benzyl-β-D-arabinofuranosyl)-5-aminopyrazolo<4,3-d>pyrimidine-7-thione (88287-87-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 71 percent / NaOH / methanol; H₂O / Heating

2: 78 percent / diphenyl phosphoryl azide, triethylamine / toluene / Heating

3: Zn, NH₄Cl / methanol / Heating

4: H₂S, triethylamine / pyridine

5: pyridine / toluene / 1.) 0 deg C, 2.) room temp.

6: NH₄OH / methanol / 100 °C

7: NaOH / methanol; H₂O / 100 °C

With pyridine; ammonium hydroxide; sodium hydroxide; diphenyl phosphoryl azide; hydrogen sulfide; ammonium chloride; triethylamine; zinc; In pyridine; methanol; water; toluene;

DOI:10.1021/jo00177a028

upstream raw materials:

Methyl 3-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-5-carbamoylpyrazole-4-carboxylate

Downstream raw materials:

3-(2,3,5-Tri-O-benzyl-β-D-arabinofuranosyl)-5-cyanopyrazole-4-carboxylic acid

3-(2,3,5-Tri-O-benzyl-β-D-arabinofuranosyl)-4-<<(2,2,2-trichloroethoxy)carbonyl>amino>pyrazole-5-carbothiamide

N-[3-((2S,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-7-thioxo-6,7-dihydro-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-benzamide

3-(2,3,5-Tri-O-benzyl-β-D-arabinofuranosyl)-4-<<(2,2,2-trichlorethoxy)carbonyl>amino>pyrazole-5-carbonitrile