Acrylic acid (1S,2R)-1-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-propyl]-2-methyl-but-3-enyl ester

Base Information

Chemical Name:Acrylic acid (1S,2R)-1-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-propyl]-2-methyl-but-3-enyl ester
CAS No.:837383-57-0
Molecular Formula:C₂₅H₄₀O₅Si
Molecular Weight:448.675
Hs Code.:

Synonyms:Acrylic acid (1S,2R)-1-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-propyl]-2-methyl-but-3-enyl ester

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Chemical Property of Acrylic acid (1S,2R)-1-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-propyl]-2-methyl-but-3-enyl ester

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Technology Process of Acrylic acid (1S,2R)-1-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-propyl]-2-methyl-but-3-enyl ester

There total 5 articles about Acrylic acid (1S,2R)-1-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-propyl]-2-methyl-but-3-enyl 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: 80.0%

: 835929-46-9
(3R,4S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-3-methyl-hept-1-en-4-ol

: 814-68-6,25189-84-8
acryloyl chloride

: 837383-57-0
Acrylic acid (1S,2R)-1-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-propyl]-2-methyl-but-3-enyl ester

Guidance literature:: With dmap; triethylamine; In dichloromethane; at -78 ℃; for 2h;
DOI:10.1021/ol0476873

Reference yield:

: 916659-56-8
(S)-3-(tert-butyldimethylsilyloxy)-4-(4-methoxybenzyloxy)butanal

: 837383-57-0
Acrylic acid (1S,2R)-1-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-propyl]-2-methyl-but-3-enyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: t-BuOK / tetrahydrofuran; hexane / 0.33 h / -45 °C

1.2: (+)-β-methoxydiisopinocampheylborane / tetrahydrofuran; hexane / 0.58 h / -78 °C

1.3: 75 percent / BF₃*Et₂O / tetrahydrofuran; hexane / 4 h / 78 °C

2.1: 80 percent / DMAP; Et₃N / CH₂Cl₂ / 2 h / -78 °C

With dmap; potassium tert-butylate; triethylamine; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ol0476873

Reference yield:

: 835929-53-8
(S)-tert-butyl({1-[(4-methoxybenzyl)oxy]pent-4-en-2-yl}oxy)dimethylsilane

: 837383-57-0
Acrylic acid (1S,2R)-1-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-propyl]-2-methyl-but-3-enyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: O₃ / CH₂Cl₂ / 0.33 h / -78 °C

1.2: PPh₃ / CH₂Cl₂ / 1 h / -78 °C

2.1: t-BuOK / tetrahydrofuran; hexane / 0.33 h / -45 °C

2.2: (+)-β-methoxydiisopinocampheylborane / tetrahydrofuran; hexane / 0.58 h / -78 °C

2.3: 75 percent / BF₃*Et₂O / tetrahydrofuran; hexane / 4 h / 78 °C

3.1: 80 percent / DMAP; Et₃N / CH₂Cl₂ / 2 h / -78 °C

With dmap; potassium tert-butylate; ozone; triethylamine; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ol0476873