2-[(2Z,4E)-6-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-hexa-2,4-dienyl]-2-((E)-5-methanesulfonyloxy-2-methoxymethoxy-pent-2-enyl)-malonic acid di-tert-butyl ester

Base Information

Chemical Name:2-[(2Z,4E)-6-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-hexa-2,4-dienyl]-2-((E)-5-methanesulfonyloxy-2-methoxymethoxy-pent-2-enyl)-malonic acid di-tert-butyl ester
CAS No.:176219-56-0
Molecular Formula:C₄₂H₆₂O₁₀SSi
Molecular Weight:787.1
Hs Code.:

2-[(2Z,4E)-6-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-hexa-2,4-dienyl]-2-((E)-5-methanesulfonyloxy-2-methoxymethoxy-pent-2-enyl)-malonic acid di-tert-butyl ester

Synonyms:2-[(2Z,4E)-6-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-hexa-2,4-dienyl]-2-((E)-5-methanesulfonyloxy-2-methoxymethoxy-pent-2-enyl)-malonic acid di-tert-butyl ester

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Chemical Property of 2-[(2Z,4E)-6-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-hexa-2,4-dienyl]-2-((E)-5-methanesulfonyloxy-2-methoxymethoxy-pent-2-enyl)-malonic acid di-tert-butyl ester

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Technology Process of 2-[(2Z,4E)-6-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-hexa-2,4-dienyl]-2-((E)-5-methanesulfonyloxy-2-methoxymethoxy-pent-2-enyl)-malonic acid di-tert-butyl ester

There total 13 articles about 2-[(2Z,4E)-6-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-hexa-2,4-dienyl]-2-((E)-5-methanesulfonyloxy-2-methoxymethoxy-pent-2-enyl)-malonic acid di-tert-butyl 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: 100.0%

: 124-63-0
methanesulfonyl chloride

: 176219-55-9
2-[(2Z,4E)-6-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-hexa-2,4-dienyl]-2-((E)-5-hydroxy-2-methoxymethoxy-pent-2-enyl)-malonic acid di-tert-butyl ester

: 176219-56-0
2-[(2Z,4E)-6-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-hexa-2,4-dienyl]-2-((E)-5-methanesulfonyloxy-2-methoxymethoxy-pent-2-enyl)-malonic acid di-tert-butyl ester

Guidance literature:: With pyridine; In dichloromethane; at 0 ℃; for 0.5h;
DOI:10.1139/v96-017

Reference yield:

: 131380-48-8
(E)-4-(t-butyldiphenylsilyl)oxy-2-butenal

: 176219-56-0
2-[(2Z,4E)-6-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-hexa-2,4-dienyl]-2-((E)-5-methanesulfonyloxy-2-methoxymethoxy-pent-2-enyl)-malonic acid di-tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) 18-crown-6-ether, KN(SiMe₃)2 / 1.) THF, toluene, -78 deg C, 10 min, 2.) THF, toluene, 30 min

2: 69 percent / (i-Bu)2AlH/toluene / CH₂Cl₂ / 1 h / -78 °C

3: 86 percent / LiCl, MeSO₂Cl, collidine / dimethylformamide / 1.5 h / Ambient temperature

4: 1.) NaH / 1.) DMF, THF, 30 min, room t., 2.) DMF, THF, 3 h, room t.

5: 83 percent / K₂CO₃ / methanol / 24 h / Ambient temperature

6: 100 percent / pyridine / CH₂Cl₂ / 0.5 h / 0 °C

With pyridine; 2,3,5-trimethyl-pyridine; 18-crown-6 ether; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; potassium carbonate; methanesulfonyl chloride; toluene; lithium chloride; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1139/v96-017

Reference yield:

: 92808-78-1
(E)-4-(tert-butyldiphenylsilyloxy)-2-buten-1-ol

: 176219-56-0
2-[(2Z,4E)-6-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-hexa-2,4-dienyl]-2-((E)-5-methanesulfonyloxy-2-methoxymethoxy-pent-2-enyl)-malonic acid di-tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 48 percent / PCC, NaOAc / tetrahydrofuran / 2 h / 25 °C

2: 1.) 18-crown-6-ether, KN(SiMe₃)2 / 1.) THF, toluene, -78 deg C, 10 min, 2.) THF, toluene, 30 min

3: 69 percent / (i-Bu)2AlH/toluene / CH₂Cl₂ / 1 h / -78 °C

4: 86 percent / LiCl, MeSO₂Cl, collidine / dimethylformamide / 1.5 h / Ambient temperature

5: 1.) NaH / 1.) DMF, THF, 30 min, room t., 2.) DMF, THF, 3 h, room t.

6: 83 percent / K₂CO₃ / methanol / 24 h / Ambient temperature

7: 100 percent / pyridine / CH₂Cl₂ / 0.5 h / 0 °C

With pyridine; 2,3,5-trimethyl-pyridine; 18-crown-6 ether; sodium acetate; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; potassium carbonate; methanesulfonyl chloride; toluene; pyridinium chlorochromate; lithium chloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1139/v96-017