Methyl 3-(3,5-di-O-benzyl-2-deoxy-β-D-erythro-pentofuranosyl)-5-cyanopyrazole-4-carboxylate

Base Information

Chemical Name:Methyl 3-(3,5-di-O-benzyl-2-deoxy-β-D-erythro-pentofuranosyl)-5-cyanopyrazole-4-carboxylate
CAS No.:88287-71-2
Molecular Formula:C₂₅H₂₅N₃O₅
Molecular Weight:447.491
Hs Code.:

Synonyms:Methyl 3-(3,5-di-O-benzyl-2-deoxy-β-D-erythro-pentofuranosyl)-5-cyanopyrazole-4-carboxylate

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Chemical Property of Methyl 3-(3,5-di-O-benzyl-2-deoxy-β-D-erythro-pentofuranosyl)-5-cyanopyrazole-4-carboxylate

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Technology Process of Methyl 3-(3,5-di-O-benzyl-2-deoxy-β-D-erythro-pentofuranosyl)-5-cyanopyrazole-4-carboxylate

There total 9 articles about Methyl 3-(3,5-di-O-benzyl-2-deoxy-β-D-erythro-pentofuranosyl)-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: 76.0%

: 88287-68-7
Methyl 3-(3,5-di-O-benzyl-2-deoxy-β-D-erythro-pentofuranosyl)-5-carbamoylpyrazole-4-carboxylate

: 88287-71-2
Methyl 3-(3,5-di-O-benzyl-2-deoxy-β-D-erythro-pentofuranosyl)-5-cyanopyrazole-4-carboxylate

Guidance literature:: With pyridine; trifluoroacetic anhydride; In tetrahydrofuran; 1,4-dioxane;
DOI:10.1021/jo00177a028

Reference yield:

: 50908-41-3
2,5-anhydro-3-deoxy-4,6-di-O-toluoyl-D-ribohexononitrile

: 88287-71-2
Methyl 3-(3,5-di-O-benzyl-2-deoxy-β-D-erythro-pentofuranosyl)-5-cyanopyrazole-4-carboxylate

Guidance literature:: Multi-step reaction with 9 steps

1: 12.1 g / sodium (trifluoroacetoxy)borohydride, HCl / tetrahydrofuran / 18 h / Ambient temperature

2: 63 percent / sodium acetate, pyridine / Ambient temperature

3: NaOCH₃ / methanol / 0.75 h / Heating

4: 59 percent / KOH / dimethylsulfoxide / 2 h / 15 - 20 °C

5: N₂O₄ / CCl₄; acetic acid / 2 h / 0 °C

6: KOH / diethyl ether; H₂O / 5.5 h / 0 °C

7: diethyl ether / 0.25 h / 0 °C

8: 37 percent / NH₃ / methanol / 48 h / 25 °C

9: 76 percent / pyridine, trifluoroacetic anhydride / dioxane; tetrahydrofuran

With pyridine; hydrogenchloride; potassium hydroxide; sodium (trifluoroacetoxy)borohydride; ammonia; sodium methylate; sodium acetate; dinitrogen tetraoxide; trifluoroacetic anhydride; In tetrahydrofuran; 1,4-dioxane; methanol; tetrachloromethane; diethyl ether; water; acetic acid; dimethyl sulfoxide;
DOI:10.1021/jo00177a028

Reference yield:

: 88287-62-1
1-Acetamido-2,5-anhydro-1,3-dideoxy-D-ribo-hexitol

: 88287-71-2
Methyl 3-(3,5-di-O-benzyl-2-deoxy-β-D-erythro-pentofuranosyl)-5-cyanopyrazole-4-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: 59 percent / KOH / dimethylsulfoxide / 2 h / 15 - 20 °C

2: N₂O₄ / CCl₄; acetic acid / 2 h / 0 °C

3: KOH / diethyl ether; H₂O / 5.5 h / 0 °C

4: diethyl ether / 0.25 h / 0 °C

5: 37 percent / NH₃ / methanol / 48 h / 25 °C

6: 76 percent / pyridine, trifluoroacetic anhydride / dioxane; tetrahydrofuran

With pyridine; potassium hydroxide; ammonia; dinitrogen tetraoxide; trifluoroacetic anhydride; In tetrahydrofuran; 1,4-dioxane; methanol; tetrachloromethane; diethyl ether; water; acetic acid; dimethyl sulfoxide;
DOI:10.1021/jo00177a028