(Rs,S)-(-)-methyl N-(tert-butanesulfinyl)-3-amino-3-(4-allyldimethylsilyl)phenylpropanoate

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Chemical Name:(Rs,S)-(-)-methyl N-(tert-butanesulfinyl)-3-amino-3-(4-allyldimethylsilyl)phenylpropanoate
CAS No.:261761-43-7
Molecular Formula:C₁₉H₃₁NO₃SSi
Molecular Weight:381.612
Hs Code.:

Synonyms:(Rs,S)-(-)-methyl N-(tert-butanesulfinyl)-3-amino-3-(4-allyldimethylsilyl)phenylpropanoate

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Chemical Property of (Rs,S)-(-)-methyl N-(tert-butanesulfinyl)-3-amino-3-(4-allyldimethylsilyl)phenylpropanoate

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Technology Process of (Rs,S)-(-)-methyl N-(tert-butanesulfinyl)-3-amino-3-(4-allyldimethylsilyl)phenylpropanoate

There total 8 articles about (Rs,S)-(-)-methyl N-(tert-butanesulfinyl)-3-amino-3-(4-allyldimethylsilyl)phenylpropanoate 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: 79.0%

: 79-20-9
acetic acid methyl ester

: 261761-41-5
(R)-(-)-N-[(4-allyldimethylsilylphenyl)methylene]-tert-butanesulfinamide

: 261761-43-7
(Rs,S)-(-)-methyl N-(tert-butanesulfinyl)-3-amino-3-(4-allyldimethylsilyl)phenylpropanoate

Guidance literature:: acetic acid methyl ester; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.25h;

With triisopropoxytitanium(IV) chloride; In tetrahydrofuran; at -78 ℃; for 0.5h;

(R)-(-)-N-[(4-allyldimethylsilylphenyl)methylene]-tert-butanesulfinamide; In tetrahydrofuran; at -78 ℃; for 3.33333h; Further stages.;
DOI:10.1021/ol9912480

Reference yield:

: 10602-01-4
p-bromobenzaldehyde 1,3-dioxolane

: 261761-43-7
(Rs,S)-(-)-methyl N-(tert-butanesulfinyl)-3-amino-3-(4-allyldimethylsilyl)phenylpropanoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: t-BuLi / tetrahydrofuran; pentane / 0.58 h / -78 °C

1.2: 91 percent / tetrahydrofuran; pentane / 1.17 h / -78 °C

2.1: 86 percent / p-TsOH / acetone / 6 h / Heating

3.1: 68 percent / Ti(OiPr)4 / tetrahydrofuran / 1 h / Heating

4.1: LDA / tetrahydrofuran / 0.25 h / -78 °C

4.2: ClTi(O-i-Pr)3 / tetrahydrofuran / 0.5 h / -78 °C

4.3: 79 percent / tetrahydrofuran / 3.33 h / -78 °C

With titanium(IV) isopropylate; tert.-butyl lithium; toluene-4-sulfonic acid; lithium diisopropyl amide; In tetrahydrofuran; acetone; pentane; 1.1: Metallation / 1.2: Substitution / 2.1: Hydrolysis / 3.1: Condensation / 4.1: Metallation / 4.2: transmetallation / 4.3: Addition;
DOI:10.1021/ol9912480

Reference yield:

: 4028-23-3
Allylchlorodimethylsilane

: 261761-43-7
(Rs,S)-(-)-methyl N-(tert-butanesulfinyl)-3-amino-3-(4-allyldimethylsilyl)phenylpropanoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-BuLi / tetrahydrofuran; various solvent(s) / 0.83 h / -78 °C

1.2: 82 percent / tetrahydrofuran / 1 h / 20 °C

2.1: t-BuLi / tetrahydrofuran; pentane / 0.67 h / -78 °C

2.2: 82 percent / tetrahydrofuran; pentane / 1 h / -78 °C

3.1: 68 percent / Ti(OiPr)4 / tetrahydrofuran / 1 h / Heating

4.1: LDA / tetrahydrofuran / 0.25 h / -78 °C

4.2: ClTi(O-i-Pr)3 / tetrahydrofuran / 0.5 h / -78 °C

4.3: 79 percent / tetrahydrofuran / 3.33 h / -78 °C

With titanium(IV) isopropylate; n-butyllithium; tert.-butyl lithium; lithium diisopropyl amide; In tetrahydrofuran; pentane; 1.1: Metallation / 1.2: Substitution / 2.1: Metallation / 2.2: Formylation / 3.1: Condensation / 4.1: Metallation / 4.2: transmetallation / 4.3: Addition;
DOI:10.1021/ol9912480