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

Base Information

• Chemical Name: (1'S,2'R,2Z,4E)-5-<1',2'-Epoxy-4',4'-(ethylendioxy)-2',6',6'-trimethylcyclohexyl>-3-methylpenta-2,4-diensaeure-methylester
• CAS No.: 122346-87-6
• Molecular Formula: C₁₈H₂₆O₅
• Molecular Weight: 322.401
• Mol file: 122346-87-6.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (1'S,2'R,2Z,4E)-5-<1',2'-Epoxy-4',4'-(ethylendioxy)-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:

ethyl 4-bromo-3-methylcrotonate (51318-62-8,51371-55-2,26918-14-9) → (1'S,2'R,2Z,4E)-5-<1',2'-Epoxy-4',4'-(ethylendioxy)-2',6',6'-trimethylcyclohexyl>-3-methylpenta-2,4-diensaeure-methylester (122346-87-6,122407-46-9,130856-57-4,132340-86-4,132340-87-5)

Guidance literature:

Multi-step reaction with 3 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

With potassium methanolate; iodine; zinc; In methanol;

DOI:10.1016/S0040-4020(01)80491-9

Reference yield: 83.0%

C18H26O5 (122346-87-6,122407-46-9,130856-57-4,132340-86-4,132340-87-5) → (+)-(S)-5-(1'-Hydroxy-2',6',6'-trimethyl-4'-oxocyclohex-2'-enyl)-3-methylpenta-2,4-diensaeure-methylester (79434-13-2,7200-31-9)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; for 48h; Ambient temperature;

DOI:10.1002/hlca.19900730426

Reference yield:

(1'S,2'R,2Z,4E)-5-<1',2'-Epoxy-4',4'-(ethylendioxy)-2',6',6'-trimethylcyclohexyl>-3-methylpenta-2,4-diensaeure-methylester (122346-87-6,122407-46-9,130856-57-4,132340-86-4,132340-87-5) → (1'S,2'R,4'S,2Z,4E)-(1',2'-epoxy-4'-hydroxy-2',6',6'-trimethylcyclohexyl)-3-methylpenta-2,4-dienal (8066-07-7,28321-44-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / aq. HClO₄ / tetrahydrofuran / 0.03 h / 4 °C

2: LiAlH₄ / tetrahydrofuran / 2 h / Ambient temperature; other reducing agent

3: 100 percent / MnO₂ / CH₂Cl₂ / 2 h / Ambient temperature

With manganese(IV) oxide; lithium aluminium tetrahydride; perchloric acid; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4020(01)80491-9

upstream raw materials:

ethyl 4-bromo-3-methylcrotonate

Downstream raw materials:

(+)-(S)-5-(1'-Hydroxy-2',6',6'-trimethyl-4'-oxocyclohex-2'-enyl)-3-methylpenta-2,4-diensaeure-methylester

(3'RS,4'S)-5-(3',4'-Diacetoxy-2',6',6'-trimethylcyclohex-1'-enyl)-3-methylpenta-2,4-diensaeure-methylester

(3'S,4'S)-5-(3',4'-Dihydroxy-2',6',6'-trimethylcyclohex-1'-enyl)-3-methylpenta-2,4-diensaeure-methylester

(3'R,4'S)-5-(3',4'-Dihydroxy-2',6',6'-trimethylcyclohex-1'-enyl)-3-methylpenta-2,4-diensaeure-methylester