((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyloxy)-acetic acid (2E,6E,10Z)-(1R,14S)-14-isopropenyl-3,7,11-trimethyl-cyclotetradeca-2,6,10-trienyl ester

Base Information

• Chemical Name: ((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyloxy)-acetic acid (2E,6E,10Z)-(1R,14S)-14-isopropenyl-3,7,11-trimethyl-cyclotetradeca-2,6,10-trienyl ester
• CAS No.: 72638-68-7
• Molecular Formula: C₃₂H₅₂O₃
• Molecular Weight: 484.763

Synonyms:

Chemical Property of ((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyloxy)-acetic acid (2E,6E,10Z)-(1R,14S)-14-isopropenyl-3,7,11-trimethyl-cyclotetradeca-2,6,10-trienyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyloxy)-acetic acid (2E,6E,10Z)-(1R,14S)-14-isopropenyl-3,7,11-trimethyl-cyclotetradeca-2,6,10-trienyl ester

There total 2 articles about ((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyloxy)-acetic acid (2E,6E,10Z)-(1R,14S)-14-isopropenyl-3,7,11-trimethyl-cyclotetradeca-2,6,10-trienyl 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:

(–)-menthyloxyacetic acid chloride (87637-47-6) + (2E,6E,10E)-(1R,14S)-14-Isopropenyl-3,7,11-trimethyl-cyclotetradeca-2,6,10-trienol (59686-17-8) → ((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyloxy)-acetic acid (2E,6E,10E)-(1S,14R)-14-isopropenyl-3,7,11-trimethyl-cyclotetradeca-2,6,10-trienyl ester (72638-68-7)

Guidance literature:

With pyridine; In benzene; Yield given; 1.) 2 h, ice cooling, 2.) r.t.;

DOI:10.1021/jo01294a041

Reference yield:

(–)-menthyloxyacetic acid chloride (87637-47-6) + (2E,6E,10Z)-14-Isopropenyl-3,7,11-trimethyl-cyclotetradeca-2,6,10-trienone (72623-61-1) → ((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyloxy)-acetic acid (2E,6E,10Z)-(1R,14S)-14-isopropenyl-3,7,11-trimethyl-cyclotetradeca-2,6,10-trienyl ester (72638-68-7,72690-76-7,87584-22-3)

Guidance literature:

With pyridine; (+)-Darvon-LiAlH₄; Multistep reaction; 1.) 0 deg C; 2.) benzene, 12 h, r.t.;

DOI:10.1246/cl.1983.1121

Reference yield: 54.0%

((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyloxy)-acetic acid (2E,6E,10Z)-(1R,14S)-14-isopropenyl-3,7,11-trimethyl-cyclotetradeca-2,6,10-trienyl ester (72638-68-7,72690-76-7,87584-22-3) → (-)-neocembrene (cembrene-A) (31570-39-5,38748-84-4,57918-06-6,71213-92-8,72690-72-3,72690-73-4,72691-72-6,73246-00-1,105662-19-9,139492-81-2)

Guidance literature:

With lithium; ethylamine; at -78 ℃;

DOI:10.1246/cl.1983.1121

upstream raw materials:

(–)-menthyloxyacetic acid chloride

(2E,6E,10E)-(1R,14S)-14-Isopropenyl-3,7,11-trimethyl-cyclotetradeca-2,6,10-trienol

(2E,6E,10Z)-14-Isopropenyl-3,7,11-trimethyl-cyclotetradeca-2,6,10-trienone

Downstream raw materials:

(-)-neocembrene (cembrene-A)

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