(2S)-[(1S,4S,5R)-4-Benzyloxymethyl-4-methylcyclopent-2-en-1-yl]propanoic acid

Base Information

Chemical Name:(2S)-[(1S,4S,5R)-4-Benzyloxymethyl-4-methylcyclopent-2-en-1-yl]propanoic acid
CAS No.:261511-35-7
Molecular Formula:C₁₇H₂₂O₃
Molecular Weight:274.36
Hs Code.:

Synonyms:(2S)-[(1S,4S,5R)-4-Benzyloxymethyl-4-methylcyclopent-2-en-1-yl]propanoic acid

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Chemical Property of (2S)-[(1S,4S,5R)-4-Benzyloxymethyl-4-methylcyclopent-2-en-1-yl]propanoic acid

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Technology Process of (2S)-[(1S,4S,5R)-4-Benzyloxymethyl-4-methylcyclopent-2-en-1-yl]propanoic acid

There total 9 articles about (2S)-[(1S,4S,5R)-4-Benzyloxymethyl-4-methylcyclopent-2-en-1-yl]propanoic 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: 91.0%

: 75-16-1
methylmagnesium bromide

: 261511-33-5
(3S,3aS,4R,6aS)-4-Benzyloxymethyl-3,3a,4,6a-tetrahydro-3-methylcyclopenta[b]furan-2-one

: 261511-35-7
(2S)-[(1S,4S,5R)-4-Benzyloxymethyl-4-methylcyclopent-2-en-1-yl]propanoic acid

Guidance literature:: With copper(I) bromide dimethylsulfide complex; dimethylsulfide; In tetrahydrofuran; at -25 ℃; for 5h;
DOI:10.1055/s-1997-3253

Reference yield:

: 144938-82-9
(1S,4R)-(+)-4-(Hydroxymethyl)cyclopent-2-enol

: 261511-35-7
(2S)-[(1S,4S,5R)-4-Benzyloxymethyl-4-methylcyclopent-2-en-1-yl]propanoic acid

Guidance literature:: Multi-step reaction with 8 steps

1.1: NaH / dimethylformamide / 0.25 h / 0 °C

1.2: 77 percent / dimethylformamide / 17 h / -60 - 20 °C

2.1: 98 percent / pyridine / CHCl₃ / 3 h / 25 °C

3.1: LDA / hexane; tetrahydrofuran; hexamethylphosphoric acid triamide / 0.33 h / -78 °C

3.2: 100 percent / hexane; tetrahydrofuran / 0.42 h / -78 - 20 °C

4.1: xylene / 18 h / 190 °C

4.2: 83 percent / NaOH; H₂O / tetrahydrofuran / 2 h

5.1: 99 percent / I₂; NaHCO₃ / acetonitrile / 24 h / 25 °C

6.1: 82 percent / DBU / tetrahydrofuran / 3 h / Heating

7.1: LDA / hexane; tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / -78 °C

7.2: 85 percent / hexane; tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / -78 °C

8.1: CuBr*Me₂S; Me₂S / tetrahydrofuran; diethyl ether / 1 h / -25 °C

8.2: tetrahydrofuran; diethyl ether / 5 h / -25 °C

8.3: 91 percent / NaOH; H₂O / tetrahydrofuran; diethyl ether / 2 h / 20 °C

With pyridine; copper(I) bromide dimethylsulfide complex; dimethylsulfide; iodine; sodium hydride; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; chloroform; N,N-dimethyl-formamide; acetonitrile; xylene; 1.1: Metallation / 1.2: Etherification / 2.1: Acetylation / 3.1: Metallation / 3.2: Etherification / 4.1: Rearrangement / 4.2: Hydrolysis / 5.1: Cyclization / 6.1: Dehydroiodination / 7.1: Metallation / 7.2: Methylation / 8.1: Metallation / 8.2: Substitution / 8.3: Hydrolysis;
DOI:10.1039/a907522d

Reference yield:

: 261511-22-2
(1S)-cis-4-Benzyloxymethylcyclopent-2-en-1-ol

: 261511-35-7
(2S)-[(1S,4S,5R)-4-Benzyloxymethyl-4-methylcyclopent-2-en-1-yl]propanoic acid

Guidance literature:: Multi-step reaction with 7 steps

1.1: 98 percent / pyridine / CHCl₃ / 3 h / 25 °C

2.1: LDA / hexane; tetrahydrofuran; hexamethylphosphoric acid triamide / 0.33 h / -78 °C

2.2: 100 percent / hexane; tetrahydrofuran / 0.42 h / -78 - 20 °C

3.1: xylene / 18 h / 190 °C

3.2: 83 percent / NaOH; H₂O / tetrahydrofuran / 2 h

4.1: 99 percent / I₂; NaHCO₃ / acetonitrile / 24 h / 25 °C

5.1: 82 percent / DBU / tetrahydrofuran / 3 h / Heating

6.1: LDA / hexane; tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / -78 °C

6.2: 85 percent / hexane; tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / -78 °C

7.1: CuBr*Me₂S; Me₂S / tetrahydrofuran; diethyl ether / 1 h / -25 °C

7.2: tetrahydrofuran; diethyl ether / 5 h / -25 °C

7.3: 91 percent / NaOH; H₂O / tetrahydrofuran; diethyl ether / 2 h / 20 °C

With pyridine; copper(I) bromide dimethylsulfide complex; dimethylsulfide; iodine; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; chloroform; acetonitrile; xylene; 1.1: Acetylation / 2.1: Metallation / 2.2: Etherification / 3.1: Rearrangement / 3.2: Hydrolysis / 4.1: Cyclization / 5.1: Dehydroiodination / 6.1: Metallation / 6.2: Methylation / 7.1: Metallation / 7.2: Substitution / 7.3: Hydrolysis;
DOI:10.1039/a907522d