(E)-3-((1S,2R,5R)-2-Isopropenyl-1-methyl-5-m-tolyl-cyclopentyl)-acrylic acid benzyl ester

Base Information

Chemical Name:(E)-3-((1S,2R,5R)-2-Isopropenyl-1-methyl-5-m-tolyl-cyclopentyl)-acrylic acid benzyl ester
CAS No.:1026693-97-9
Molecular Formula:C₂₆H₃₀O₂
Molecular Weight:374.523
Hs Code.:

Synonyms:(E)-3-((1S,2R,5R)-2-Isopropenyl-1-methyl-5-m-tolyl-cyclopentyl)-acrylic acid benzyl ester

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Chemical Property of (E)-3-((1S,2R,5R)-2-Isopropenyl-1-methyl-5-m-tolyl-cyclopentyl)-acrylic acid benzyl ester

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Technology Process of (E)-3-((1S,2R,5R)-2-Isopropenyl-1-methyl-5-m-tolyl-cyclopentyl)-acrylic acid benzyl ester

There total 6 articles about (E)-3-((1S,2R,5R)-2-Isopropenyl-1-methyl-5-m-tolyl-cyclopentyl)-acrylic acid 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:

: 775343-67-4
(1S,2R,5R)-2-isopropenyl-1-methyl-5-m-tolylcyclopentanecarbaldehyde

: 65946-45-4
2-(Trimethylsilyl)ethansaeure-benzylester

: 1026693-97-9
(E)-3-((1S,2R,5R)-2-Isopropenyl-1-methyl-5-m-tolyl-cyclopentyl)-acrylic acid benzyl ester

Guidance literature:: 2-(Trimethylsilyl)ethansaeure-benzylester; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.5h;

(1S,2R,5R)-2-isopropenyl-1-methyl-5-m-tolylcyclopentanecarbaldehyde; In tetrahydrofuran; at -25 ℃; for 2h;
DOI:10.1021/jo049351c

Reference yield:

: 775343-66-3
((1S,2R,5R)-2-isopropenyl-1-methyl-5-m-tolylcyclopentyl)methanol

: 1026693-97-9
(E)-3-((1S,2R,5R)-2-Isopropenyl-1-methyl-5-m-tolyl-cyclopentyl)-acrylic acid benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 77 percent / NaOAc; PCC; 4 Angstroem molecular sieves / CH₂Cl₂ / 2.5 h / 0 °C

2.1: LDA / tetrahydrofuran / 0.5 h / -78 °C

2.2: tetrahydrofuran / 2 h / -25 °C

With 4 A molecular sieve; sodium acetate; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; 2.2: Peterson olefination;
DOI:10.1021/jo049351c

Reference yield:

: 775343-72-1
(1R,2R,5R)-2-acetyl-1-methyl-5-m-tolylcyclopentanecarboxylic acid ethyl ester

: 1026693-97-9
(E)-3-((1S,2R,5R)-2-Isopropenyl-1-methyl-5-m-tolyl-cyclopentyl)-acrylic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: DBU / 36 h / 20 °C

2.1: 76 percent / tetrahydrofuran / 10 h / -78 - 20 °C

3.1: 93 percent / DIBALH / hexane; toluene / 3 h / -78 - -30 °C

4.1: 77 percent / NaOAc; PCC; 4 Angstroem molecular sieves / CH₂Cl₂ / 2.5 h / 0 °C

5.1: LDA / tetrahydrofuran / 0.5 h / -78 °C

5.2: tetrahydrofuran / 2 h / -25 °C

With 4 A molecular sieve; sodium acetate; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; toluene; 5.2: Peterson olefination;
DOI:10.1021/jo049351c