(4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-isopropyl-3-methyl-cyclopent-2-enone

Base Information

Chemical Name:(4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-isopropyl-3-methyl-cyclopent-2-enone
CAS No.:862846-93-3
Molecular Formula:C₁₅H₂₈O₂Si
Molecular Weight:268.472
Hs Code.:

Synonyms:(4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-isopropyl-3-methyl-cyclopent-2-enone

Suppliers and Price of (4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-isopropyl-3-methyl-cyclopent-2-enone

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-isopropyl-3-methyl-cyclopent-2-enone

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-isopropyl-3-methyl-cyclopent-2-enone

There total 1 articles about (4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-isopropyl-3-methyl-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:

: 59995-48-1
(R)-4-acetoxycyclopent-2-en-1-one

: 862846-93-3
(4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-isopropyl-3-methyl-cyclopent-2-enone

Guidance literature:: Multi-step reaction with 4 steps

1.1: TMSCl; CuBr*DMS; HMPA / tetrahydrofuran / -78 - -40 °C

1.2: (1R)-10-camphorsulfonic acid / CH₂Cl₂ / 20 h / Heating

2.1: CuI; TMSCl / diethyl ether / 17 h / -40 - 20 °C

2.2: Pd(OAc)2 / acetonitrile / 9 h / 20 °C

3.1: 724 mg / (i-Pr)2NEt; n-BuLi; (1R)-(10-camphorsulfonyl)oxaziridine / tetrahydrofuran; hexane / -78 - -30 °C

4.1: 81 percent / imidazole / dimethylformamide / 16.17 h / 0 - 20 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide; n-butyllithium; chloro-trimethyl-silane; copper(I) bromide dimethylsulfide complex; (1R)-(?)-(10-camphorsulfonyl)oxaziridine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; hexane; N,N-dimethyl-formamide; 2.2: Saegusa oxidation;
DOI:10.1021/ol047387l

Reference yield: 50.0%

: 862846-93-3
(4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-isopropyl-3-methyl-cyclopent-2-enone

: 862846-97-7
tert-Butyl-[(4R,7R)-7-(2-iodo-ethyl)-7-methyl-4,5,6,7-tetrahydro-isobenzofuran-4-yloxy]-diphenyl-silane

: 862846-98-8
(2R,3S,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-{2-[(4S,7R)-7-(tert-butyl-diphenyl-silanyloxy)-4-methyl-4,5,6,7-tetrahydro-isobenzofuran-4-yl]-ethyl}-3-isopropyl-4-methyl-cyclopentanone

Guidance literature:: With boron trifluoride diethyl etherate; tert.-butyl lithium; thien-2-yl(cyano)copper lithium; In tetrahydrofuran; diethyl ether; pentane; at -78 - -40 ℃; for 1h;
DOI:10.1021/ol047387l

Reference yield:

: 862846-93-3
(4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-isopropyl-3-methyl-cyclopent-2-enone

: 9-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxy)-8-isopropyl-5a,7a-dimethyl-3,4,5,5a,6,7,7a,8,9,10a-decahydro-1-oxa-benzo[cd]cyclopenta[h]azulen-10-one

Guidance literature:: Multi-step reaction with 4 steps

1: 50 percent / t-BuLi; (2-thienyl)Cu(CN)Li; BF₃*Et₂O / pentane; diethyl ether; tetrahydrofuran / 1 h / -78 - -40 °C

2: 93 percent / LDA; HMPA; Et₃N / tetrahydrofuran; hexane / -78 - 20 °C

3: 70 percent / LiClO₄; 2,6-lutidine / CH₂Cl₂ / 17 h / 20 °C / Electrochemical reaction

4: 85 percent / aq. HCl / tetrahydrofuran / 2 h / 20 °C

With 2,6-dimethylpyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; boron trifluoride diethyl etherate; tert.-butyl lithium; lithium perchlorate; thien-2-yl(cyano)copper lithium; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; pentane;
DOI:10.1021/ol047387l