coronatine benzyl ester

Base Information

• Chemical Name: coronatine benzyl ester
• CAS No.: 189506-61-4
• Molecular Formula: C₂₅H₃₁NO₄
• Molecular Weight: 409.525
• Mol file: 189506-61-4.mol

Synonyms:coronatine benzyl ester

Chemical Property of coronatine benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of coronatine benzyl ester

There total 15 articles about coronatine benzyl ester 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: 89.0%

(+)-coronafacic acid (62251-98-3) + (1S,2S)-1-Amino-2-ethyl-cyclopropanecarboxylic acid benzyl ester; compound with trifluoro-acetic acid → coronatine benzyl ester (189506-61-4)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; for 24h; Ambient temperature;

DOI:10.1016/S0040-4020(97)00614-5

Reference yield:

(S)-(+)-ethyl 4-oxocyclopent-2-ene acetate (107932-04-7) → coronatine benzyl ester (189506-61-4)

Guidance literature:

Multi-step reaction with 7 steps

1: H₂ / Pd-C / ethanol / 24 h / Ambient temperature

2: 85 percent / PPTS / benzene / 24 h / Heating

4: 94 percent / aq. p-TsOH / acetone / 24 h / Ambient temperature

5: NaH / ethanol / 0 deg C to rt

6: 70 percent / aq. HCl / Heating

7: 89 percent / Et₃N, DMAP, EtN=C=N(CH₂)3NMe₂*HCl / CH₂Cl₂ / 24 h / Ambient temperature

With hydrogenchloride; dmap; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; palladium on activated charcoal; In ethanol; dichloromethane; acetone; benzene;

DOI:10.1016/S0040-4020(97)00614-5

Reference yield:

((1S)-4-oxocyclopent-2-enyl)acetic acid (132665-05-5) → coronatine benzyl ester (189506-61-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 91 percent / NaHCO₃ / dimethylformamide / 6 h / Ambient temperature

2: H₂ / Pd-C / ethanol / 24 h / Ambient temperature

3: 85 percent / PPTS / benzene / 24 h / Heating

5: 94 percent / aq. p-TsOH / acetone / 24 h / Ambient temperature

6: NaH / ethanol / 0 deg C to rt

7: 70 percent / aq. HCl / Heating

8: 89 percent / Et₃N, DMAP, EtN=C=N(CH₂)3NMe₂*HCl / CH₂Cl₂ / 24 h / Ambient temperature

With hydrogenchloride; dmap; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; palladium on activated charcoal; In ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1016/S0040-4020(97)00614-5

upstream raw materials:

(+)-coronafacic acid

(S)-(+)-ethyl 4-oxocyclopent-2-ene acetate

((1S)-4-oxocyclopent-2-enyl)acetic acid

(S)-3-di(ethoxycarbonyl)methyl-1-cyclopentanone

Downstream raw materials:

(+)-coronatine

Refernces

• 1、 Nara, Shinji,Toshima, Hiroaki,Ichihara, Akitami. "Asymmetric total syntheses of (+)-coronafacic acid and (+)-coronatine, phytotoxins isolated from Pseudomonas Syringae pathovars". . p. 9509 - 9524. Retrieved 2007/10/03.