(+)-(1S,5S)-3-methyl-5-(3-phenyl-allyloxycarbonylamino)-cyclopent-2-enecarboxylic acid

Base Information

Chemical Name:(+)-(1S,5S)-3-methyl-5-(3-phenyl-allyloxycarbonylamino)-cyclopent-2-enecarboxylic acid
CAS No.:939962-93-3
Molecular Formula:C₁₇H₁₉NO₄
Molecular Weight:301.342
Hs Code.:

Synonyms:(+)-(1S,5S)-3-methyl-5-(3-phenyl-allyloxycarbonylamino)-cyclopent-2-enecarboxylic acid

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Chemical Property of (+)-(1S,5S)-3-methyl-5-(3-phenyl-allyloxycarbonylamino)-cyclopent-2-enecarboxylic acid

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Technology Process of (+)-(1S,5S)-3-methyl-5-(3-phenyl-allyloxycarbonylamino)-cyclopent-2-enecarboxylic acid

There total 4 articles about (+)-(1S,5S)-3-methyl-5-(3-phenyl-allyloxycarbonylamino)-cyclopent-2-enecarboxylic 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: 75.0%

: 939962-91-1
(-)-(1R,5S)-3-methyl-5-(3-phenyl-allyloxycarbonylamino)-cyclopent-2-enecarboxylic acid 3-phenyl-allyl ester

: (+)-(1R,5S)-3-methyl-5-(3-phenyl-allyloxycarbonylamino)-cyclopent-2-enecarboxylic acid

: 939962-93-3
(+)-(1S,5S)-3-methyl-5-(3-phenyl-allyloxycarbonylamino)-cyclopent-2-enecarboxylic acid

Guidance literature:: With potassium hydroxide; In methanol; water; at 50 ℃; for 2h;
DOI:10.1016/j.tetasy.2007.02.019

Reference yield:

: 5-methyl-4,6a-dihydro-3aH-cyclopenta[c]furan-1,3-dione

: 939962-93-3
(+)-(1S,5S)-3-methyl-5-(3-phenyl-allyloxycarbonylamino)-cyclopent-2-enecarboxylic acid

Guidance literature:: Multi-step reaction with 2 steps

1.1: quinine / toluene / 8 h / -15 °C

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

1.3: 9.0 g / toluene / Heating

2.1: 75 percent / potassium hydroxide / methanol; H₂O / 2 h / 50 °C

With potassium hydroxide; Quinine; In methanol; water; toluene; 1.2: Curtius rearrangement;
DOI:10.1016/j.tetasy.2007.02.019

Reference yield:

: 139228-09-4
5-methylenetetrahydrocyclopenta[c]furan-1,3-dione

: 939962-93-3
(+)-(1S,5S)-3-methyl-5-(3-phenyl-allyloxycarbonylamino)-cyclopent-2-enecarboxylic acid

Guidance literature:: Multi-step reaction with 3 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: 9.0 g / toluene / Heating

3.1: 75 percent / potassium hydroxide / methanol; H₂O / 2 h / 50 °C

With potassium hydroxide; toluene-4-sulfonic acid; Quinine; In methanol; water; toluene; 2.2: Curtius rearrangement;
DOI:10.1016/j.tetasy.2007.02.019