[1-acetoxy-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohexyl]-acetic acid tert-butyl ester

Base Information

Chemical Name:[1-acetoxy-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohexyl]-acetic acid tert-butyl ester
CAS No.:274901-13-2
Molecular Formula:C₂₇H₅₂O₆Si₂
Molecular Weight:528.877
Hs Code.:

[1-acetoxy-3,5-bis-(<i>tert</i>-butyl-dimethyl-silanyloxy)-2-methylene-cyclohexyl]-acetic acid <i>tert</i>-butyl ester

Synonyms:[1-acetoxy-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohexyl]-acetic acid tert-butyl ester

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Chemical Property of [1-acetoxy-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohexyl]-acetic acid tert-butyl ester

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Technology Process of [1-acetoxy-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohexyl]-acetic acid tert-butyl ester

There total 6 articles about [1-acetoxy-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohexyl]-acetic acid 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: 33.0%

: 108-24-7
acetic anhydride

: 273402-79-2
[3,5-bis-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-2-oxo-cyclohexyl]-acetic acid tert-butyl ester

: 74-95-3
1,1-dibromomethane

: 274901-13-2
[1-acetoxy-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohexyl]-acetic acid tert-butyl ester

Guidance literature:: [3,5-bis-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-2-oxo-cyclohexyl]-acetic acid tert-butyl ester; 1,1-dibromomethane; With titanium tetrachloride; zinc; In tetrahydrofuran; at 20 ℃; for 4h;

acetic anhydride; With scandium tris(trifluoromethanesulfonate); at 20 ℃; for 12h;
DOI:10.1016/S0040-4039(00)00169-6

Reference yield:

: 5292-43-3
bromoacetic acid tert-butyl ester

: 274901-13-2
[1-acetoxy-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohexyl]-acetic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 91 percent / Zn; (MeO)3B / tetrahydrofuran / 20 °C / Heating

2.1: 100 percent / imidazole / dimethylformamide / 12 h / 20 °C

3.1: 94 percent / oxalyl chloride

4.1: Zn; TiCl₄ / tetrahydrofuran / 4 h / 20 °C

4.2: 33 percent / Sc(OTf)3 / 12 h / 20 °C

With 1H-imidazole; oxalyl dichloride; Trimethyl borate; titanium tetrachloride; zinc; In tetrahydrofuran; N,N-dimethyl-formamide; 1.1: Reformatsky reaction / 2.1: silylation / 3.1: Swern oxidation / 4.1: Substitution / 4.2: Acetylation;
DOI:10.1016/S0040-4039(00)00169-6

Reference yield:

: 199613-48-4
5-tert-butyl-dimethylsilyloxy-(5S)-2-cyclohexenone

: 274901-13-2
[1-acetoxy-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohexyl]-acetic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 80 percent / OsO₄; NMO / acetone; H₂O / 24 h / 20 °C

2.1: 91 percent / Zn; (MeO)3B / tetrahydrofuran / 20 °C / Heating

3.1: 100 percent / imidazole / dimethylformamide / 12 h / 20 °C

4.1: 94 percent / oxalyl chloride

5.1: Zn; TiCl₄ / tetrahydrofuran / 4 h / 20 °C

5.2: 33 percent / Sc(OTf)3 / 12 h / 20 °C

With 1H-imidazole; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; Trimethyl borate; titanium tetrachloride; zinc; In tetrahydrofuran; water; N,N-dimethyl-formamide; acetone; 1.1: dihydroxylation / 2.1: Reformatsky reaction / 3.1: silylation / 4.1: Swern oxidation / 5.1: Substitution / 5.2: Acetylation;
DOI:10.1016/S0040-4039(00)00169-6