(1'S,2'R,4'S,2Z,4E)-5-(1',2'-Epoxy-4'-hydroxy-2',6',6'-trimethylcyclohexyl)-3-methylpenta-2,4-diensaeure-methylester

Base Information

Chemical Name:(1'S,2'R,4'S,2Z,4E)-5-(1',2'-Epoxy-4'-hydroxy-2',6',6'-trimethylcyclohexyl)-3-methylpenta-2,4-diensaeure-methylester
CAS No.:69297-03-6
Molecular Formula:C₁₆H₂₄O₄
Molecular Weight:280.364
Hs Code.:

Synonyms:(1'S,2'R,4'S,2Z,4E)-5-(1',2'-Epoxy-4'-hydroxy-2',6',6'-trimethylcyclohexyl)-3-methylpenta-2,4-diensaeure-methylester

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Chemical Property of (1'S,2'R,4'S,2Z,4E)-5-(1',2'-Epoxy-4'-hydroxy-2',6',6'-trimethylcyclohexyl)-3-methylpenta-2,4-diensaeure-methylester

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Technology Process of (1'S,2'R,4'S,2Z,4E)-5-(1',2'-Epoxy-4'-hydroxy-2',6',6'-trimethylcyclohexyl)-3-methylpenta-2,4-diensaeure-methylester

There total 2 articles about (1'S,2'R,4'S,2Z,4E)-5-(1',2'-Epoxy-4'-hydroxy-2',6',6'-trimethylcyclohexyl)-3-methylpenta-2,4-diensaeure-methylester 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:

: 51318-62-8,51371-55-2,26918-14-9
ethyl 4-bromo-3-methylcrotonate

: 69297-03-6
(1'S,2'R,4'S,2Z,4E)-5-(1',2'-Epoxy-4'-hydroxy-2',6',6'-trimethylcyclohexyl)-3-methylpenta-2,4-diensaeure-methylester

Guidance literature:: Multi-step reaction with 5 steps

1: 1) Zn, I₂ / 1) THF, 0 deg C, 10 min, 2) THF, 30 min

2: 100 percent / CH₃OK / methanol / 18 h / Ambient temperature

4: 86 percent / aq. HClO₄ / tetrahydrofuran / 0.03 h / 4 °C

5: NaBH₄ / tetrahydrofuran / 2 h / -78 °C / other reducing agents

With sodium tetrahydroborate; perchloric acid; potassium methanolate; iodine; zinc; In tetrahydrofuran; methanol;
DOI:10.1016/S0040-4020(01)80491-9

Reference yield:

: 186581-53-3,908094-01-9,334-88-3
diazomethane

: 88852-29-3
(-)-(2Z,4E)-5-(1',2'-epoxy-2',6',6'-trimethylcyclohexyl)-3-methyl-2,4-pentadienoic acid

: 69297-03-6
(1'S,2'R,4'S,2Z,4E)-5-(1',2'-Epoxy-4'-hydroxy-2',6',6'-trimethylcyclohexyl)-3-methylpenta-2,4-diensaeure-methylester

: (+/-)-(2Z,4E)-methyl 1',2'-dihydroxy-1',2'-dihydro-β-ionylideneacetate

Guidance literature:: With sodium hydroxide; Yield given. Multistep reaction. Yields of byproduct given; 1.) water solution is metabolized by the suspension of mycelia of Cerospora cruenta, 2 d; 2.) ether;
DOI:10.1016/S0031-9422(00)83100-3

Reference yield:

: 69297-03-6
(1'S,2'R,4'S,2Z,4E)-5-(1',2'-Epoxy-4'-hydroxy-2',6',6'-trimethylcyclohexyl)-3-methylpenta-2,4-diensaeure-methylester

: 8066-07-7,28321-44-0
(1'S,2'R,4'S,2Z,4E)-(1',2'-epoxy-4'-hydroxy-2',6',6'-trimethylcyclohexyl)-3-methylpenta-2,4-dienal

Guidance literature:: Multi-step reaction with 2 steps

1: 83 percent / LiAlH₄ / tetrahydrofuran / 0.17 h / -25 °C

2: 92 percent / MnO₂ / diethyl ether / 5 h / 20 °C

With manganese(IV) oxide; lithium aluminium tetrahydride; In tetrahydrofuran; diethyl ether;
DOI:10.1246/cl.2002.1248