ethyl (1R,5S)-5-(5-tert-butyldiphenyl-silyloxy-1-penten-2-yl)-1-methyl-2-oxo-cyclopentanecarboxylate

Base Information

Chemical Name:ethyl (1R,5S)-5-(5-tert-butyldiphenyl-silyloxy-1-penten-2-yl)-1-methyl-2-oxo-cyclopentanecarboxylate
CAS No.:172374-02-6
Molecular Formula:C₃₀H₄₀O₄Si
Molecular Weight:492.731
Hs Code.:

Synonyms:ethyl (1R,5S)-5-(5-tert-butyldiphenyl-silyloxy-1-penten-2-yl)-1-methyl-2-oxo-cyclopentanecarboxylate

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Chemical Property of ethyl (1R,5S)-5-(5-tert-butyldiphenyl-silyloxy-1-penten-2-yl)-1-methyl-2-oxo-cyclopentanecarboxylate

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Technology Process of ethyl (1R,5S)-5-(5-tert-butyldiphenyl-silyloxy-1-penten-2-yl)-1-methyl-2-oxo-cyclopentanecarboxylate

There total 6 articles about ethyl (1R,5S)-5-(5-tert-butyldiphenyl-silyloxy-1-penten-2-yl)-1-methyl-2-oxo-cyclopentanecarboxylate 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: 95.0%

: 172374-01-5
ethyl (1S,5R)-5-<(5-tert-butyldiphenylsilyloxy)-1-penten-2-yl>-2-oxo-cyclopentanecarboxylate

: 74-88-4
methyl iodide

: 172374-02-6
ethyl (1R,5S)-5-(5-tert-butyldiphenyl-silyloxy-1-penten-2-yl)-1-methyl-2-oxo-cyclopentanecarboxylate

Guidance literature:: With potassium hexamethylsilazane; In tetrahydrofuran; toluene; -78 deg C, 1 h; -78 to 20 deg C; 2 h;
DOI:10.1016/0040-4020(95)00834-U

Reference yield:

: 64180-78-5
4-bromopent-4-en-1-ol

: 172374-02-6
ethyl (1R,5S)-5-(5-tert-butyldiphenyl-silyloxy-1-penten-2-yl)-1-methyl-2-oxo-cyclopentanecarboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 79 percent / imidazole / dimethylformamide / 3 h / 20 °C

2: 1.) tBuLi, 0.25 M lithium 2-thienylcyanocuprate / 1.) THF, -78 deg C, 2 h; -78 deg C, 1 h, 2.) THF, -78 deg C, 2 h

3: 93 percent / Ti(OEt)4 / 96 h / Heating

4: 95 percent / 0.50 M KN(SiMe₃)2 / toluene; tetrahydrofuran / -78 deg C, 1 h; -78 to 20 deg C; 2 h

With 1H-imidazole; titanium(IV) tetraethanolate; tert.-butyl lithium; potassium hexamethylsilazane; thien-2-yl(cyano)copper lithium; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;
DOI:10.1016/0040-4020(95)00834-U

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 172374-02-6
ethyl (1R,5S)-5-(5-tert-butyldiphenyl-silyloxy-1-penten-2-yl)-1-methyl-2-oxo-cyclopentanecarboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 79 percent / imidazole / dimethylformamide / 3 h / 20 °C

2: 1.) tBuLi, 0.25 M lithium 2-thienylcyanocuprate / 1.) THF, -78 deg C, 2 h; -78 deg C, 1 h, 2.) THF, -78 deg C, 2 h

3: 93 percent / Ti(OEt)4 / 96 h / Heating

4: 95 percent / 0.50 M KN(SiMe₃)2 / toluene; tetrahydrofuran / -78 deg C, 1 h; -78 to 20 deg C; 2 h

With 1H-imidazole; titanium(IV) tetraethanolate; tert.-butyl lithium; potassium hexamethylsilazane; thien-2-yl(cyano)copper lithium; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;
DOI:10.1016/0040-4020(95)00834-U