ethyl (+)-(2E,4E,6Z,8E)-3,7-dimethyl-9-[(3R,6S)-6-isopropyl-3-methylcyclohex-1-en-1-yl]nona-2,4,6,8-tetraenoate

Base Information

Chemical Name:ethyl (+)-(2E,4E,6Z,8E)-3,7-dimethyl-9-[(3R,6S)-6-isopropyl-3-methylcyclohex-1-en-1-yl]nona-2,4,6,8-tetraenoate
CAS No.:1093863-59-2
Molecular Formula:C₂₃H₃₄O₂
Molecular Weight:342.522
Hs Code.:

Synonyms:ethyl (+)-(2E,4E,6Z,8E)-3,7-dimethyl-9-[(3R,6S)-6-isopropyl-3-methylcyclohex-1-en-1-yl]nona-2,4,6,8-tetraenoate

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Chemical Property of ethyl (+)-(2E,4E,6Z,8E)-3,7-dimethyl-9-[(3R,6S)-6-isopropyl-3-methylcyclohex-1-en-1-yl]nona-2,4,6,8-tetraenoate

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Technology Process of ethyl (+)-(2E,4E,6Z,8E)-3,7-dimethyl-9-[(3R,6S)-6-isopropyl-3-methylcyclohex-1-en-1-yl]nona-2,4,6,8-tetraenoate

There total 3 articles about ethyl (+)-(2E,4E,6Z,8E)-3,7-dimethyl-9-[(3R,6S)-6-isopropyl-3-methylcyclohex-1-en-1-yl]nona-2,4,6,8-tetraenoate 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: 71.0%

: (-)-menthone tosylhydrazone

: 252930-80-6
(2E,4E,6Z,8E)-9-Iodo-3,7-dimethyl-nona-2,4,6,8-tetraenoic acid ethyl ester

: 1093863-59-2
ethyl (+)-(2E,4E,6Z,8E)-3,7-dimethyl-9-[(3R,6S)-6-isopropyl-3-methylcyclohex-1-en-1-yl]nona-2,4,6,8-tetraenoate

Guidance literature:: (-)-menthone tosylhydrazone; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 0 ℃;

With Triisopropyl borate; In tetrahydrofuran; hexane; at -78 - 20 ℃;

(2E,4E,6Z,8E)-9-Iodo-3,7-dimethyl-nona-2,4,6,8-tetraenoic acid ethyl ester; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; TlOH; In tetrahydrofuran; hexane; water; at 25 ℃; for 0.5h;
DOI:10.1016/j.bmc.2008.09.069

Reference yield: 70.0%

: 125950-36-9
1-(((trifluoromethyl)sulfonyl)oxy)-3(R)-methyl-6(S)-isopropylcyclohexene

: ethyl (2E,4E,6Z,8E)-3,7-dimethyl-9-(tri-n-butylstannyl)-nona-2,4,6,8-tetraenoate

: 1093863-59-2
ethyl (+)-(2E,4E,6Z,8E)-3,7-dimethyl-9-[(3R,6S)-6-isopropyl-3-methylcyclohex-1-en-1-yl]nona-2,4,6,8-tetraenoate

Guidance literature:: With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; triphenyl-arsane; cesium fluoride; In N,N-dimethyl-formamide; at 45 ℃; Inert atmosphere;
DOI:10.1016/j.bmc.2011.03.033

Reference yield:

: 10458-14-7,14073-97-3,17627-49-5,7786-64-3
(2R,5S)-menthone

: 1093863-59-2
ethyl (+)-(2E,4E,6Z,8E)-3,7-dimethyl-9-[(3R,6S)-6-isopropyl-3-methylcyclohex-1-en-1-yl]nona-2,4,6,8-tetraenoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere

1.2: Inert atmosphere

2.1: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; triphenyl-arsane; cesium fluoride / N,N-dimethyl-formamide / 45 °C / Inert atmosphere

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; n-butyllithium; triphenyl-arsane; diisopropylamine; cesium fluoride; In tetrahydrofuran; N,N-dimethyl-formamide; 2.1: Stille coupling;
DOI:10.1016/j.bmc.2011.03.033