2-[(Z)-6-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-hex-3-enyl]-2-[(2Z,4E)-2-methyl-6-(tetrahydro-pyran-2-yloxy)-hexa-2,4-dienyl]-malonic acid dimethyl ester

Base Information

• Chemical Name: 2-[(Z)-6-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-hex-3-enyl]-2-[(2Z,4E)-2-methyl-6-(tetrahydro-pyran-2-yloxy)-hexa-2,4-dienyl]-malonic acid dimethyl ester
• CAS No.: 151806-06-3
• Molecular Formula: C₄₀H₅₆O₇Si
• Molecular Weight: 676.966
• Mol file: 151806-06-3.mol

Synonyms:

Chemical Property of 2-[(Z)-6-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-hex-3-enyl]-2-[(2Z,4E)-2-methyl-6-(tetrahydro-pyran-2-yloxy)-hexa-2,4-dienyl]-malonic acid dimethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(Z)-6-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-hex-3-enyl]-2-[(2Z,4E)-2-methyl-6-(tetrahydro-pyran-2-yloxy)-hexa-2,4-dienyl]-malonic acid dimethyl ester

There total 6 articles about 2-[(Z)-6-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-hex-3-enyl]-2-[(2Z,4E)-2-methyl-6-(tetrahydro-pyran-2-yloxy)-hexa-2,4-dienyl]-malonic acid dimethyl 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:

(3Z)-3-methyl-6-tert-butyldiphenylsilyloxy-3-hexen-1-ol (150919-50-9) → 2-[(Z)-6-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-hex-3-enyl]-2-[(2Z,4E)-2-methyl-6-(tetrahydro-pyran-2-yloxy)-hexa-2,4-dienyl]-malonic acid dimethyl ester (151806-06-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

2: 1.) NaH, 2.) KI / 1.) DMF, THF, 0 deg C, 1 h, 2.) DMF, THF, 70 deg C, 36 h

3: 1.) NaH / 1.) THF, from 0 deg C to RT, 75 min, 2.) THF, DMF, RT, 16.5 h

With sodium hydride; triethylamine; potassium iodide; In dichloromethane;

DOI:10.1139/v93-153

Reference yield:

(3E/3Z)-3-methyl-6-tert-butyldiphenylsilyloxy-1-tetrahydropyranyloxy-3-hexene → 2-[(Z)-6-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-hex-3-enyl]-2-[(2Z,4E)-2-methyl-6-(tetrahydro-pyran-2-yloxy)-hexa-2,4-dienyl]-malonic acid dimethyl ester (151806-06-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 355 mg / pyridinium p-toluenesulfonate (PPTS), i-PrOH / 4 h / 80 °C

2: 93 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

3: 1.) NaH, 2.) KI / 1.) DMF, THF, 0 deg C, 1 h, 2.) DMF, THF, 70 deg C, 36 h

4: 1.) NaH / 1.) THF, from 0 deg C to RT, 75 min, 2.) THF, DMF, RT, 16.5 h

With pyridinium p-toluenesulfonate; sodium hydride; triethylamine; isopropyl alcohol; potassium iodide; In dichloromethane;

DOI:10.1139/v93-153

Reference yield:

(2Z,4E)-2-Methyl-6-(tetrahydro-pyran-2-yloxy)-hexa-2,4-dien-1-ol (151806-13-2) → 2-[(Z)-6-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-hex-3-enyl]-2-[(2Z,4E)-2-methyl-6-(tetrahydro-pyran-2-yloxy)-hexa-2,4-dienyl]-malonic acid dimethyl ester (151806-06-3)

Guidance literature:

Multi-step reaction with 2 steps

1: LiCl, s-collidine, methanesulfonyl chloride / dimethylformamide / 2 h / 0 - 25 °C

2: 1.) NaH / 1.) THF, from 0 deg C to RT, 75 min, 2.) THF, DMF, RT, 16.5 h

With 2,4,6-trimethyl-pyridine; sodium hydride; methanesulfonyl chloride; lithium chloride; In N,N-dimethyl-formamide;

DOI:10.1139/v93-153

upstream raw materials:

2-((2E,4Z)-6-Chloro-5-methyl-hexa-2,4-dienyloxy)-tetrahydro-pyran

2-[(Z)-6-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-hex-3-enyl]-malonic acid dimethyl ester

(3Z)-3-methyl-6-tert-butyldiphenylsilyloxy-3-hexen-1-ol

(2Z,4E)-2-Methyl-6-(tetrahydro-pyran-2-yloxy)-hexa-2,4-dien-1-ol