(+)-(1S,2R)-4-methylene-2-[(2E)-3-phenyl-2-propenyloxycarbonyl]cyclopentanecarboxylic acid

Base Information

Chemical Name:(+)-(1S,2R)-4-methylene-2-[(2E)-3-phenyl-2-propenyloxycarbonyl]cyclopentanecarboxylic acid
CAS No.:198022-60-5
Molecular Formula:C₁₇H₁₈O₄
Molecular Weight:286.328
Hs Code.:

Synonyms:(+)-(1S,2R)-4-methylene-2-[(2E)-3-phenyl-2-propenyloxycarbonyl]cyclopentanecarboxylic acid

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (+)-(1S,2R)-4-methylene-2-[(2E)-3-phenyl-2-propenyloxycarbonyl]cyclopentanecarboxylic acid

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Technology Process of (+)-(1S,2R)-4-methylene-2-[(2E)-3-phenyl-2-propenyloxycarbonyl]cyclopentanecarboxylic acid

There total 11 articles about (+)-(1S,2R)-4-methylene-2-[(2E)-3-phenyl-2-propenyloxycarbonyl]cyclopentanecarboxylic 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: 96.0%

: 4407-36-7
(2E)-3-phenyl-2-propen-1-ol

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

: 198022-61-6
(+)-(1R,2S)-4-methylene-2-[(2E)-3-phenyl-2-propenyloxycarbonyl]cyclopentanecarboxylic acid

: 198022-60-5
(+)-(1S,2R)-4-methylene-2-[(2E)-3-phenyl-2-propenyloxycarbonyl]cyclopentanecarboxylic acid

Guidance literature:: With 9-O-propargylquinine; In toluene; at -10 ℃; for 8h; Temperature; Time; enantioselective reaction;
DOI:10.1021/op700023h

Reference yield: 85.0%

: 4407-36-7
(2E)-3-phenyl-2-propen-1-ol

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

: 198022-60-5
(+)-(1S,2R)-4-methylene-2-[(2E)-3-phenyl-2-propenyloxycarbonyl]cyclopentanecarboxylic acid

Guidance literature:: With 9-O-propargylquinine; In toluene; at -10 ℃; for 8h; Temperature; Time; enantioselective reaction; Large scale;
DOI:10.1021/op700023h

Reference yield:

: 4534-68-3
1,2,3,4-butanetetracarboxylic acid

: 198022-60-5
(+)-(1S,2R)-4-methylene-2-[(2E)-3-phenyl-2-propenyloxycarbonyl]cyclopentanecarboxylic acid

Guidance literature:: Multi-step reaction with 8 steps

1: H₂SO₄

2: NaOMe / methanol

3: aq. HCl

4: H₂SO₄

5: KOtBu / tetrahydrofuran

6: aq. KOH / tetrahydrofuran

7: 75 percent / (EtCO)2O / 135 °C

8: 84 percent / quinine / toluene / 4 h / -15 °C

With hydrogenchloride; potassium hydroxide; sulfuric acid; potassium tert-butylate; sodium methylate; propionic acid anhydride; Quinine; In tetrahydrofuran; methanol; toluene;
DOI:10.1016/S0960-894X(02)00958-7