Acetic acid, bromo-, (1R,2Z)-1-[(1R)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-methylethyl]-4- [[(1,1-dimethylethyl)diphenylsilyl]oxy]-3-methyl-2-butenyl ester

Base Information

Chemical Name:Acetic acid, bromo-, (1R,2Z)-1-[(1R)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-methylethyl]-4- [[(1,1-dimethylethyl)diphenylsilyl]oxy]-3-methyl-2-butenyl ester
CAS No.:877833-46-0
Molecular Formula:C32H49BrO4Si2
Molecular Weight:633.814
Hs Code.:

Acetic acid, bromo-,
(1R,2Z)-1-[(1R)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-methylethyl]-4-
[[(1,1-dimethylethyl)diphenylsilyl]oxy]-3-methyl-2-butenyl ester

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Chemical Property of Acetic acid, bromo-, (1R,2Z)-1-[(1R)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-methylethyl]-4- [[(1,1-dimethylethyl)diphenylsilyl]oxy]-3-methyl-2-butenyl ester

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Technology Process of Acetic acid, bromo-, (1R,2Z)-1-[(1R)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-methylethyl]-4- [[(1,1-dimethylethyl)diphenylsilyl]oxy]-3-methyl-2-butenyl ester

There total 7 articles about Acetic acid, bromo-, (1R,2Z)-1-[(1R)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-methylethyl]-4- [[(1,1-dimethylethyl)diphenylsilyl]oxy]-3-methyl-2-butenyl 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: 85.0%

: 877833-45-9
1-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-2,5-dimethyl-hex-4-en-3-ol

: 598-21-0
2-Bromoacetyl bromide

: 877833-46-0
bromo-acetic acid 1-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-4-(tert-butyl-diphenyl-silanyloxy)-3-methyl-but-2-enyl ester

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 ℃; for 2h;
DOI:10.1016/j.tetlet.2005.11.156

Reference yield:

: 877833-42-6
4-(tert-butyl-diphenyl-silanyloxy)-3-methyl-but-2-enal

: 877833-46-0
bromo-acetic acid 1-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-4-(tert-butyl-diphenyl-silanyloxy)-3-methyl-but-2-enyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-BuBOTf; Et₃N / CH₂Cl₂ / 0.83 h / -55 - 0 °C

1.2: 90 percent / CH₂Cl₂ / 4 h / -70 °C

2.1: 88 percent / NaBH₄ / tetrahydrofuran; H₂O / 3.5 h / 20 °C

3.1: 80 percent / Et₃N; 4-dimethylaminopyridine / CH₂Cl₂ / 12 h

4.1: 85 percent / Et₃N; 4-dimethylaminopyridine / CH₂Cl₂ / 2 h / 0 °C

With dmap; sodium tetrahydroborate; n-BuBOTf; triethylamine; In tetrahydrofuran; dichloromethane; water;
DOI:10.1016/j.tetlet.2005.11.156

Reference yield:

: 877833-53-9
4-(tert-butyl-diphenyl-silanyloxy)-3-methyl-but-2-en-1-ol

: 877833-46-0
bromo-acetic acid 1-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-4-(tert-butyl-diphenyl-silanyloxy)-3-methyl-but-2-enyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 96 percent / tetrapropylammonium perruthenate; 4-methyl-morpholine-N-oxide / CH₂Cl₂ / 2 h / 0 °C

2.1: n-BuBOTf; Et₃N / CH₂Cl₂ / 0.83 h / -55 - 0 °C

2.2: 90 percent / CH₂Cl₂ / 4 h / -70 °C

3.1: 88 percent / NaBH₄ / tetrahydrofuran; H₂O / 3.5 h / 20 °C

4.1: 80 percent / Et₃N; 4-dimethylaminopyridine / CH₂Cl₂ / 12 h

5.1: 85 percent / Et₃N; 4-dimethylaminopyridine / CH₂Cl₂ / 2 h / 0 °C

With dmap; sodium tetrahydroborate; tetrapropylammonium perruthennate; n-BuBOTf; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; dichloromethane; water;
DOI:10.1016/j.tetlet.2005.11.156