2-[(2Z,4E)-6-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-hexa-2,4-dienyl]-2-((Z)-6-methanesulfonyloxy-3-methyl-hex-3-enyl)-malonic acid dimethyl ester

Base Information

Chemical Name:2-[(2Z,4E)-6-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-hexa-2,4-dienyl]-2-((Z)-6-methanesulfonyloxy-3-methyl-hex-3-enyl)-malonic acid dimethyl ester
CAS No.:151805-95-7
Molecular Formula:C₃₆H₅₀O₈SSi
Molecular Weight:670.94
Hs Code.:

2-[(2Z,4E)-6-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-hexa-2,4-dienyl]-2-((Z)-6-methanesulfonyloxy-3-methyl-hex-3-enyl)-malonic acid dimethyl ester

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Chemical Property of 2-[(2Z,4E)-6-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-hexa-2,4-dienyl]-2-((Z)-6-methanesulfonyloxy-3-methyl-hex-3-enyl)-malonic acid dimethyl ester

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Technology Process of 2-[(2Z,4E)-6-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-hexa-2,4-dienyl]-2-((Z)-6-methanesulfonyloxy-3-methyl-hex-3-enyl)-malonic acid dimethyl ester

There total 11 articles about 2-[(2Z,4E)-6-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-hexa-2,4-dienyl]-2-((Z)-6-methanesulfonyloxy-3-methyl-hex-3-enyl)-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:

: 150919-50-9
(3Z)-3-methyl-6-tert-butyldiphenylsilyloxy-3-hexen-1-ol

: 151805-95-7
2-[(2Z,4E)-6-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-hexa-2,4-dienyl]-2-((Z)-6-methanesulfonyloxy-3-methyl-hex-3-enyl)-malonic acid dimethyl ester

Guidance literature:: Multi-step reaction with 5 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: 74 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2.5 h / Ambient temperature

4: 83 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

5: 1.) NaH / 1.) THF, from 0 deg C to RT, 75 min, 2.) THF, DMF, RT, 15 h

With tetrabutyl ammonium fluoride; sodium hydride; triethylamine; potassium iodide; In tetrahydrofuran; dichloromethane;
DOI:10.1139/v93-153

Reference yield:

: (3E/3Z)-3-methyl-6-tert-butyldiphenylsilyloxy-1-tetrahydropyranyloxy-3-hexene

: 151805-95-7
2-[(2Z,4E)-6-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-hexa-2,4-dienyl]-2-((Z)-6-methanesulfonyloxy-3-methyl-hex-3-enyl)-malonic acid dimethyl ester

Guidance literature:: Multi-step reaction with 6 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: 74 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2.5 h / Ambient temperature

5: 83 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

6: 1.) NaH / 1.) THF, from 0 deg C to RT, 75 min, 2.) THF, DMF, RT, 15 h

With tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydride; triethylamine; isopropyl alcohol; potassium iodide; In tetrahydrofuran; dichloromethane;
DOI:10.1139/v93-153

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 151805-95-7
2-[(2Z,4E)-6-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-hexa-2,4-dienyl]-2-((Z)-6-methanesulfonyloxy-3-methyl-hex-3-enyl)-malonic acid dimethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 99 percent / imidazole / tetrahydrofuran / 1 h / 0 °C

2: 86 percent / pyridinium p-toluenesulfonate (PPTS), i-PrOH / 4 h / 80 °C

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

4: 1.) NaH / 1.) THF, from 0 deg C to RT, 75 min, 2.) THF, DMF, RT, 15 h

With 1H-imidazole; 2,4,6-trimethyl-pyridine; pyridinium p-toluenesulfonate; sodium hydride; methanesulfonyl chloride; isopropyl alcohol; lithium chloride; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1139/v93-153