methyl (E)-5-((tert-butyldimethylsilyl)oxy)-5-(3,5-dimethylphenyl)pent-2-enoate

Base Information

Chemical Name:methyl (E)-5-((tert-butyldimethylsilyl)oxy)-5-(3,5-dimethylphenyl)pent-2-enoate
CAS No.:1268623-55-7
Molecular Formula:C₂₀H₃₂O₃Si
Molecular Weight:348.558
Hs Code.:

Synonyms:methyl (E)-5-((tert-butyldimethylsilyl)oxy)-5-(3,5-dimethylphenyl)pent-2-enoate

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Chemical Property of methyl (E)-5-((tert-butyldimethylsilyl)oxy)-5-(3,5-dimethylphenyl)pent-2-enoate

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Technology Process of methyl (E)-5-((tert-butyldimethylsilyl)oxy)-5-(3,5-dimethylphenyl)pent-2-enoate

There total 3 articles about methyl (E)-5-((tert-butyldimethylsilyl)oxy)-5-(3,5-dimethylphenyl)pent-2-enoate 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: 81.0%

: 5779-95-3
3,5-dimethylbenzaldehyde

: 107174-33-4
tert-butyl(((E)-1-methoxybuta-1,3-dien-1-yl)oxy)dimethylsilane

: 1268623-55-7
methyl (E)-5-((tert-butyldimethylsilyl)oxy)-5-(3,5-dimethylphenyl)pent-2-enoate

Guidance literature:: With 3,3’-bis[3,5-bis(perfluoropropan-2-yl)phenyl]-1,1’-binaphthalene-2,2’-sulfonimide; In diethyl ether; at -78 ℃; for 72h; optical yield given as %ee; enantiospecific reaction;
DOI:10.1002/anie.201005954

Reference yield:

: 623-43-8,4358-59-2,18707-60-3,130981-57-6
methyl crotonate

: 1268623-55-7
methyl (E)-5-((tert-butyldimethylsilyl)oxy)-5-(3,5-dimethylphenyl)pent-2-enoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium diisopropyl amide / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

1.2: 2 h / -78 - 20 °C / Inert atmosphere

2.1: 3,3’-bis[3,5-bis(perfluoropropan-2-yl)phenyl]-1,1’-binaphthalene-2,2’-sulfonimide / diethyl ether / 72 h / -78 °C

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 3,3’-bis[3,5-bis(perfluoropropan-2-yl)phenyl]-1,1’-binaphthalene-2,2’-sulfonimide; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; 2.1: vinylogous Mukaiyama aldol reaction;
DOI:10.1002/anie.201005954

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1268623-55-7
methyl (E)-5-((tert-butyldimethylsilyl)oxy)-5-(3,5-dimethylphenyl)pent-2-enoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium diisopropyl amide / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

1.2: 2 h / -78 - 20 °C / Inert atmosphere

2.1: 3,3’-bis[3,5-bis(perfluoropropan-2-yl)phenyl]-1,1’-binaphthalene-2,2’-sulfonimide / diethyl ether / 72 h / -78 °C

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 3,3’-bis[3,5-bis(perfluoropropan-2-yl)phenyl]-1,1’-binaphthalene-2,2’-sulfonimide; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; 2.1: vinylogous Mukaiyama aldol reaction;
DOI:10.1002/anie.201005954