3-(3,5-Di-O-benzyl-2-deoxy-β-D-erythro-pentofuranosyl)-5-cyanopyrazole-4-carboxylic acid

Base Information

Chemical Name:3-(3,5-Di-O-benzyl-2-deoxy-β-D-erythro-pentofuranosyl)-5-cyanopyrazole-4-carboxylic acid
CAS No.:88287-74-5
Molecular Formula:C₂₄H₂₃N₃O₅
Molecular Weight:433.464
Hs Code.:

Synonyms:3-(3,5-Di-O-benzyl-2-deoxy-β-D-erythro-pentofuranosyl)-5-cyanopyrazole-4-carboxylic acid

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Chemical Property of 3-(3,5-Di-O-benzyl-2-deoxy-β-D-erythro-pentofuranosyl)-5-cyanopyrazole-4-carboxylic acid

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Technology Process of 3-(3,5-Di-O-benzyl-2-deoxy-β-D-erythro-pentofuranosyl)-5-cyanopyrazole-4-carboxylic acid

There total 10 articles about 3-(3,5-Di-O-benzyl-2-deoxy-β-D-erythro-pentofuranosyl)-5-cyanopyrazole-4-carboxylic acid 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: 81.0%

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

: 88287-74-5
3-(3,5-Di-O-benzyl-2-deoxy-β-D-erythro-pentofuranosyl)-5-cyanopyrazole-4-carboxylic acid

Guidance literature:: With sodium hydroxide; In methanol; water; Heating;
DOI:10.1021/jo00177a028

Reference yield:

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

: 88287-74-5
3-(3,5-Di-O-benzyl-2-deoxy-β-D-erythro-pentofuranosyl)-5-cyanopyrazole-4-carboxylic acid

Guidance literature:: Multi-step reaction with 10 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

10: 81 percent / NaOH / methanol; H₂O / Heating

With pyridine; hydrogenchloride; potassium hydroxide; sodium 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

: 88287-74-5
3-(3,5-Di-O-benzyl-2-deoxy-β-D-erythro-pentofuranosyl)-5-cyanopyrazole-4-carboxylic acid

Guidance literature:: Multi-step reaction with 7 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

7: 81 percent / NaOH / methanol; H₂O / Heating

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