methyl (1'S,2Z,4E,4'S)-5-(1,4-dihydroxy-2,6,6-trimethyl-2-cyclohexen-1-yl)-3-methyl-2,4-pentadien-1-ol

Base Information

• Chemical Name: methyl (1'S,2Z,4E,4'S)-5-(1,4-dihydroxy-2,6,6-trimethyl-2-cyclohexen-1-yl)-3-methyl-2,4-pentadien-1-ol
• CAS No.: 69350-40-9
• Molecular Formula: C₁₅H₂₄O₃
• Molecular Weight: 252.354
• Mol file: 69350-40-9.mol

Synonyms:methyl (1'S,2Z,4E,4'S)-5-(1,4-dihydroxy-2,6,6-trimethyl-2-cyclohexen-1-yl)-3-methyl-2,4-pentadien-1-ol

Chemical Property of methyl (1'S,2Z,4E,4'S)-5-(1,4-dihydroxy-2,6,6-trimethyl-2-cyclohexen-1-yl)-3-methyl-2,4-pentadien-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (1'S,2Z,4E,4'S)-5-(1,4-dihydroxy-2,6,6-trimethyl-2-cyclohexen-1-yl)-3-methyl-2,4-pentadien-1-ol

There total 6 articles about methyl (1'S,2Z,4E,4'S)-5-(1,4-dihydroxy-2,6,6-trimethyl-2-cyclohexen-1-yl)-3-methyl-2,4-pentadien-1-ol 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: 87.0%

(2Z,4E)-5-<(S)-1-Hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl>-3-methylpenta-2,4-dienal (41944-86-9) → methyl (1'S,2Z,4E,4'S)-5-(1,4-dihydroxy-2,6,6-trimethyl-2-cyclohexen-1-yl)-3-methyl-2,4-pentadien-1-ol (69350-40-9) + (+)-abscisyl alcohol (56298-25-0) + (1S,4R)-1-((1E,3Z)-5-Hydroxy-3-methyl-penta-1,3-dienyl)-2,6,6-trimethyl-cyclohex-2-ene-1,4-diol

Guidance literature:

With sodium tetrahydroborate; In methanol; dichloromethane; at -78 ℃; for 3h; Yields of byproduct given;

DOI:10.1080/00397919708006821

Reference yield: 39.0%

(S)-methyl abscisate (6901-90-2,6901-96-8,14398-52-8,15734-36-8,15734-37-9,20496-94-0,30816-18-3,60102-39-8,79434-13-2,93164-18-2,132340-88-6,132488-74-5,7200-31-9) → methyl (1'S,2Z,4E,4'S)-5-(1,4-dihydroxy-2,6,6-trimethyl-2-cyclohexen-1-yl)-3-methyl-2,4-pentadien-1-ol (69350-40-9) + (1S,4R)-1-((1E,3Z)-5-Hydroxy-3-methyl-penta-1,3-dienyl)-2,6,6-trimethyl-cyclohex-2-ene-1,4-diol

Guidance literature:

With diisobutylaluminium hydride; In diethyl ether; toluene; at -20 - -10 ℃; for 0.5h;

DOI:10.1080/00397919708006821

Reference yield:

Abscisic acid (2228-72-0,6755-41-5,7773-56-0,14375-45-2,14398-53-9,14674-85-2,40331-02-0,52392-36-6,72029-68-6,72029-69-7,113349-29-4,21293-29-8) → methyl (1'S,2Z,4E,4'S)-5-(1,4-dihydroxy-2,6,6-trimethyl-2-cyclohexen-1-yl)-3-methyl-2,4-pentadien-1-ol (69350-40-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) oxalyl chloride, 2.) NaBH₄ / 1.) DMF, CH₂Cl₂, 10-15 deg C, 30 min, 2.) THF, DMF, -55 deg C, 2.5 h

2: 84 percent / MnO₂ / ethyl acetate; petroleum ether / 1 h / Ambient temperature

3: NaBH₄ / methanol; CH₂Cl₂ / 3 h / -78 °C

With manganese(IV) oxide; sodium tetrahydroborate; oxalyl dichloride; In methanol; dichloromethane; ethyl acetate; Petroleum ether;

DOI:10.1080/00397919708006821

upstream raw materials:

(1S,4S)-1-((Z)-5-Hydroxy-3-methyl-pent-3-en-1-ynyl)-2,6,6-trimethyl-cyclohex-2-ene-1,4-diol

(S)-methyl abscisate

(2Z,4E)-5-<(S)-1-Hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl>-3-methylpenta-2,4-dienal

Abscisic acid

Downstream raw materials:

(2Z,4E)-5-<(S)-1-Hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl>-3-methylpenta-2,4-dienal

Abscisic acid