(-)-(1R,2R)-4-methyl-2-(3-phenyl-allyloxycarbonylamino)-cyclopent-4-enecarboxylic acid 3-phenyl-allyl ester

Base Information

• Chemical Name: (-)-(1R,2R)-4-methyl-2-(3-phenyl-allyloxycarbonylamino)-cyclopent-4-enecarboxylic acid 3-phenyl-allyl ester
• CAS No.: 939962-90-0
• Molecular Formula: C₂₆H₂₇NO₄
• Molecular Weight: 417.505
• Mol file: 939962-90-0.mol

Synonyms:(-)-(1R,2R)-4-methyl-2-(3-phenyl-allyloxycarbonylamino)-cyclopent-4-enecarboxylic acid 3-phenyl-allyl ester

Chemical Property of (-)-(1R,2R)-4-methyl-2-(3-phenyl-allyloxycarbonylamino)-cyclopent-4-enecarboxylic acid 3-phenyl-allyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(1R,2R)-4-methyl-2-(3-phenyl-allyloxycarbonylamino)-cyclopent-4-enecarboxylic acid 3-phenyl-allyl ester

There total 3 articles about (-)-(1R,2R)-4-methyl-2-(3-phenyl-allyloxycarbonylamino)-cyclopent-4-enecarboxylic acid 3-phenyl-allyl 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:

5-methyl-4,6a-dihydro-3aH-cyclopenta[c]furan-1,3-dione + (2E)-3-phenyl-2-propen-1-ol (4407-36-7) → (-)-(1R,5S)-3-methyl-5-(3-phenyl-allyloxycarbonylamino)-cyclopent-2-enecarboxylic acid 3-phenyl-allyl ester (939962-91-1) + (-)-(1R,2R)-4-methyl-2-(3-phenyl-allyloxycarbonylamino)-cyclopent-4-enecarboxylic acid 3-phenyl-allyl ester (939962-90-0)

Guidance literature:

5-methyl-4,6a-dihydro-3aH-cyclopenta[c]furan-1,3-dione; With Quinine; In toluene; at -15 ℃; for 8h;

With diphenyl phosphoryl azide; triethylamine; In toluene; at 20 - 90 ℃; for 3h;

(2E)-3-phenyl-2-propen-1-ol; In toluene; Heating;

DOI:10.1016/j.tetasy.2007.02.019

Reference yield:

5-methylenetetrahydrocyclopenta[c]furan-1,3-dione (139228-09-4) → (-)-(1R,2R)-4-methyl-2-(3-phenyl-allyloxycarbonylamino)-cyclopent-4-enecarboxylic acid 3-phenyl-allyl ester (939962-90-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 87 percent / p-TsOH / toluene / 4 h / Heating

2.1: quinine / toluene / 8 h / -15 °C

2.2: diphenyl phosphoryl azide; triethylamine / toluene / 3 h / 20 - 90 °C

2.3: toluene / Heating

With toluene-4-sulfonic acid; Quinine; In toluene; 2.2: Curtius rearrangement;

DOI:10.1016/j.tetasy.2007.02.019

Reference yield:

trans-4-methylene-1,2-cyclopentanedicarboxylic acid → (-)-(1R,2R)-4-methyl-2-(3-phenyl-allyloxycarbonylamino)-cyclopent-4-enecarboxylic acid 3-phenyl-allyl ester (939962-90-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: (EtCO)2O / 135 °C

2.1: 87 percent / p-TsOH / toluene / 4 h / Heating

3.1: quinine / toluene / 8 h / -15 °C

3.2: diphenyl phosphoryl azide; triethylamine / toluene / 3 h / 20 - 90 °C

3.3: toluene / Heating

With toluene-4-sulfonic acid; propionic acid anhydride; Quinine; In toluene; 3.2: Curtius rearrangement;

DOI:10.1016/j.tetasy.2007.02.019

upstream raw materials:

(2E)-3-phenyl-2-propen-1-ol

5-methylenetetrahydrocyclopenta[c]furan-1,3-dione

Downstream raw materials:

(-)-(1R,2R)-2-amino-4-methyl-cyclopent-3-enecarboxylic acid