(2Z,4E)-5-[(1S,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-2,2,6-trimethyl-cyclohexyl]-3-methyl-penta-2,4-dienoic acid methyl ester

Base Information

• Chemical Name: (2Z,4E)-5-[(1S,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-2,2,6-trimethyl-cyclohexyl]-3-methyl-penta-2,4-dienoic acid methyl ester
• CAS No.: 152041-08-2
• Molecular Formula: C₂₂H₄₀O₄Si
• Molecular Weight: 396.643
• Mol file: 152041-08-2.mol

Synonyms:

Chemical Property of (2Z,4E)-5-[(1S,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-2,2,6-trimethyl-cyclohexyl]-3-methyl-penta-2,4-dienoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2Z,4E)-5-[(1S,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-2,2,6-trimethyl-cyclohexyl]-3-methyl-penta-2,4-dienoic acid methyl ester

There total 1 articles about (2Z,4E)-5-[(1S,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-2,2,6-trimethyl-cyclohexyl]-3-methyl-penta-2,4-dienoic acid methyl 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:

(R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-((Z)-5-hydroxy-3-methyl-pent-3-en-1-ynyl)-2,2,6-trimethyl-cyclohexanol → (2Z,4E)-5-[(1S,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-2,2,6-trimethyl-cyclohexyl]-3-methyl-penta-2,4-dienoic acid methyl ester (152041-08-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 54 percent / Redal / tetrahydrofuran; toluene / 0.5 h / 0 °C

2: 1.) MnO₂, 2.) MnO₂, NaCN / 1.) acetone, room temperature, 30 min, 2.) HOAc, room temperature, 4 h

With manganese(IV) oxide; sodium cyanide; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; toluene;

DOI:10.1016/S0031-9422(00)90687-3

Reference yield:

(2Z,4E)-5-[(1S,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-2,2,6-trimethyl-cyclohexyl]-3-methyl-penta-2,4-dienoic acid methyl ester (152041-08-2) → (+)-1-(1E,3Z)-(1S,4R,6S)-1-(4-carbomethoxy-3-methyl-1,3-butadienyl)-2,2,6-trimethylcyclohexan-1,4-diol (152203-18-4)

Guidance literature:

In water; acetic acid; at 70 ℃; for 1.5h; Yield given;

DOI:10.1016/S0031-9422(00)90687-3

Reference yield:

(2Z,4E)-5-[(1S,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-2,2,6-trimethyl-cyclohexyl]-3-methyl-penta-2,4-dienoic acid methyl ester (152041-08-2) → (+)-1-(1E,3Z)-(1S,4R,6S)-1-(4-carboxy-3-methyl-1,3-butadienyl)-2,2,6-trimethylcyclohexan-1,4-diol

Guidance literature:

Multi-step reaction with 2 steps

1: acetic acid; H₂O / 1.5 h / 70 °C

2: 100 percent / 2 M KOH / methanol / 6 h / Ambient temperature

With potassium hydroxide; In methanol; water; acetic acid;

DOI:10.1016/S0031-9422(00)90687-3

Downstream raw materials:

(+)-1-(1E,3Z)-(1S,4R,6S)-1-(4-carbomethoxy-3-methyl-1,3-butadienyl)-2,2,6-trimethylcyclohexan-1,4-diol