4-tert-butyloxycarbonyl-5-cyano-3-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)pyrazole

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Chemical Name:4-tert-butyloxycarbonyl-5-cyano-3-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)pyrazole
CAS No.:117452-53-6
Molecular Formula:C₃₅H₃₇N₃O₆
Molecular Weight:595.695
Hs Code.:

Synonyms:4-tert-butyloxycarbonyl-5-cyano-3-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)pyrazole

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Chemical Property of 4-tert-butyloxycarbonyl-5-cyano-3-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)pyrazole

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Technology Process of 4-tert-butyloxycarbonyl-5-cyano-3-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)pyrazole

There total 8 articles about 4-tert-butyloxycarbonyl-5-cyano-3-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)pyrazole 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: 67.0%

: 117452-52-5
3-((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-5-carbamoyl-1H-pyrazole-4-carboxylic acid tert-butyl ester

: 117452-53-6
4-tert-butyloxycarbonyl-5-cyano-3-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)pyrazole

Guidance literature:: With pyridine; trifluoroacetic anhydride; In 1,4-dioxane; 1.) 0 deg C, 1 h 25 min; 2.) room temp., overnight;
DOI:10.1016/0008-6215(88)84056-4

Reference yield:

: 82267-01-4
(2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-carbonitrile

: 117452-53-6
4-tert-butyloxycarbonyl-5-cyano-3-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)pyrazole

Guidance literature:: Multi-step reaction with 8 steps

1: 79 percent / KOH (20percent) / methanol / 3 h / Heating

2: SOCl₂, N,N-dimethylformamide / diethyl ether / 1 h / Heating

3: toluene / 1.5 h / 80 °C

4: benzene / 3 h / 0 - 20 °C

5: 64 percent / toluene / 48 h / 65 °C

6: 98 percent / triethylamine / toluene / 3 h / Ambient temperature

7: 99 percent / methanol; H₂O / 120 h

8: 67 percent / trifluoroacetic anhydride-pyridine / dioxane / 1.) 0 deg C, 1 h 25 min; 2.) room temp., overnight

With pyridine; potassium hydroxide; thionyl chloride; triethylamine; N,N-dimethyl-formamide; trifluoroacetic anhydride; In 1,4-dioxane; methanol; diethyl ether; water; toluene; benzene;
DOI:10.1016/0008-6215(88)84056-4

Reference yield:

: (2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-carbonyl chloride

: 117452-53-6
4-tert-butyloxycarbonyl-5-cyano-3-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)pyrazole

Guidance literature:: Multi-step reaction with 6 steps

1: toluene / 1.5 h / 80 °C

2: benzene / 3 h / 0 - 20 °C

3: 64 percent / toluene / 48 h / 65 °C

4: 98 percent / triethylamine / toluene / 3 h / Ambient temperature

5: 99 percent / methanol; H₂O / 120 h

6: 67 percent / trifluoroacetic anhydride-pyridine / dioxane / 1.) 0 deg C, 1 h 25 min; 2.) room temp., overnight

With pyridine; triethylamine; trifluoroacetic anhydride; In 1,4-dioxane; methanol; water; toluene; benzene;
DOI:10.1016/0008-6215(88)84056-4