4-(tert-butyldimethylsilyloxy)-3-((tert-butyldiphenylsilyloxy)methyl)-5-methylene-4-(3-oxobutyl)cyclopent-2-enone

Base Information

Chemical Name:4-(tert-butyldimethylsilyloxy)-3-((tert-butyldiphenylsilyloxy)methyl)-5-methylene-4-(3-oxobutyl)cyclopent-2-enone
CAS No.:1384870-53-4
Molecular Formula:C₃₃H₄₆O₄Si₂
Molecular Weight:562.897
Hs Code.:

Synonyms:4-(tert-butyldimethylsilyloxy)-3-((tert-butyldiphenylsilyloxy)methyl)-5-methylene-4-(3-oxobutyl)cyclopent-2-enone

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Chemical Property of 4-(tert-butyldimethylsilyloxy)-3-((tert-butyldiphenylsilyloxy)methyl)-5-methylene-4-(3-oxobutyl)cyclopent-2-enone

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Technology Process of 4-(tert-butyldimethylsilyloxy)-3-((tert-butyldiphenylsilyloxy)methyl)-5-methylene-4-(3-oxobutyl)cyclopent-2-enone

There total 2 articles about 4-(tert-butyldimethylsilyloxy)-3-((tert-butyldiphenylsilyloxy)methyl)-5-methylene-4-(3-oxobutyl)cyclopent-2-enone 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: 92.0%

: 1384870-51-2
4-(tert-butyldimethylsilyloxy)-3-((tert-butyldiphenylsilyloxy)methyl)-4-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)-5-methylenecyclopent-2-enone

: 1384870-53-4
4-(tert-butyldimethylsilyloxy)-3-((tert-butyldiphenylsilyloxy)methyl)-5-methylene-4-(3-oxobutyl)cyclopent-2-enone

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In water; acetonitrile; at 40 ℃; for 4h;
DOI:10.1021/ol301513h

Reference yield:

: 1384870-50-1
4-(tert-butyldimethylsilyloxy)-3-((tert-butyldiphenylsilyloxy)methyl)-4-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)cyclopent-2-enone

: 1384870-53-4
4-(tert-butyldimethylsilyloxy)-3-((tert-butyldiphenylsilyloxy)methyl)-5-methylene-4-(3-oxobutyl)cyclopent-2-enone

Guidance literature:: Multi-step reaction with 2 steps

1.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; benzene / 3 h / -78 °C / Inert atmosphere

1.2: 2.5 h / -78 - 20 °C / Inert atmosphere

1.3: 1 h

2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / water; acetonitrile / 4 h / 40 °C

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; n-heptane; water; acetonitrile; benzene;
DOI:10.1021/ol301513h

Reference yield: 10.0%

: 1384870-53-4
4-(tert-butyldimethylsilyloxy)-3-((tert-butyldiphenylsilyloxy)methyl)-5-methylene-4-(3-oxobutyl)cyclopent-2-enone

: 3a-(tert-butyldimethylsilyloxy)-3-((tert-butyldiphenylsilyloxy)methyl)-6-hydroxy-6a-(iodomethyl)-6-methyl-4,5,6,6a-tetrahydropentalen-1(3aH)-one

: 3a-(tert-butyldimethylsilyloxy)-3-((tert-butyldiphenylsilyloxy)methyl)-6-hydroxy-6a-(iodomethyl)-6-methyl-4,5,6,6a-tetrahydropentalen-1(3aH)-one

Guidance literature:: With titanium tetrachloride; tetra-(n-butyl)ammonium iodide; In dichloromethane; at 0 ℃; for 0.25h; optical yield given as %de; Inert atmosphere;
DOI:10.1021/ol301513h