[(1R,2S)-2-(4-Methoxy-benzyloxy)-1-((S)-1-methyl-2-triisopropylsilanyloxy-ethyl)-pent-4-enyloxy]-acetic acid

Base Information

Chemical Name:[(1R,2S)-2-(4-Methoxy-benzyloxy)-1-((S)-1-methyl-2-triisopropylsilanyloxy-ethyl)-pent-4-enyloxy]-acetic acid
CAS No.:911237-08-6
Molecular Formula:C₂₇H₄₆O₆Si
Molecular Weight:494.744
Hs Code.:

Synonyms:[(1R,2S)-2-(4-Methoxy-benzyloxy)-1-((S)-1-methyl-2-triisopropylsilanyloxy-ethyl)-pent-4-enyloxy]-acetic acid

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Chemical Property of [(1R,2S)-2-(4-Methoxy-benzyloxy)-1-((S)-1-methyl-2-triisopropylsilanyloxy-ethyl)-pent-4-enyloxy]-acetic acid

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Technology Process of [(1R,2S)-2-(4-Methoxy-benzyloxy)-1-((S)-1-methyl-2-triisopropylsilanyloxy-ethyl)-pent-4-enyloxy]-acetic acid

There total 6 articles about [(1R,2S)-2-(4-Methoxy-benzyloxy)-1-((S)-1-methyl-2-triisopropylsilanyloxy-ethyl)-pent-4-enyloxy]-acetic acid 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: 92.0%

: 911237-07-5
(2S,3R,4S)-4-(4-Methoxy-benzyloxy)-2-methyl-1-triisopropylsilanyloxy-hept-6-en-3-ol

: 79-08-3
bromoacetic acid

: 911237-08-6
[(1R,2S)-2-(4-Methoxy-benzyloxy)-1-((S)-1-methyl-2-triisopropylsilanyloxy-ethyl)-pent-4-enyloxy]-acetic acid

Guidance literature:: bromoacetic acid; With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; at 0 ℃; for 0.166667h;

(2S,3R,4S)-4-(4-Methoxy-benzyloxy)-2-methyl-1-triisopropylsilanyloxy-hept-6-en-3-ol; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 15h;
DOI:10.1021/ol0615782

Reference yield:

: 947619-70-7
(S)-2-(4-methoxybenzyloxy)pent-4-enal

: 911237-08-6
[(1R,2S)-2-(4-Methoxy-benzyloxy)-1-((S)-1-methyl-2-triisopropylsilanyloxy-ethyl)-pent-4-enyloxy]-acetic acid

Guidance literature:: Multi-step reaction with 4 steps

1.1: TiCl₄; (-)-sparteine; N-methylpyrrolidinone / CH₂Cl₂ / 0 °C

1.2: CH₂Cl₂ / -78 - -30 °C

2.1: 10.3 g / NaBH₄ / tetrahydrofuran; H₂O / 1 h / 20 °C

3.1: 97 percent / imidazole / CH₂Cl₂ / 15 h / 20 °C

4.1: NaH / tetrahydrofuran; dimethylformamide / 0.17 h / 0 °C

4.2: 92 percent / tetrahydrofuran; dimethylformamide / 15 h / 20 °C

With 1H-imidazole; 1-methyl-pyrrolidin-2-one; sodium tetrahydroborate; titanium tetrachloride; sodium hydride; (-)-sparteine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ol0615782

Reference yield:

: 911237-04-2
(2S)-2-(4-methoxybenzyloxy)-4-pentenol

: 911237-08-6
[(1R,2S)-2-(4-Methoxy-benzyloxy)-1-((S)-1-methyl-2-triisopropylsilanyloxy-ethyl)-pent-4-enyloxy]-acetic acid

Guidance literature:: Multi-step reaction with 5 steps

1.1: (COCl)2; DMSO / CH₂Cl₂ / 0.5 h / -78 - -65 °C

2.1: TiCl₄; (-)-sparteine; N-methylpyrrolidinone / CH₂Cl₂ / 0 °C

2.2: CH₂Cl₂ / -78 - -30 °C

3.1: 10.3 g / NaBH₄ / tetrahydrofuran; H₂O / 1 h / 20 °C

4.1: 97 percent / imidazole / CH₂Cl₂ / 15 h / 20 °C

5.1: NaH / tetrahydrofuran; dimethylformamide / 0.17 h / 0 °C

5.2: 92 percent / tetrahydrofuran; dimethylformamide / 15 h / 20 °C

With 1H-imidazole; 1-methyl-pyrrolidin-2-one; sodium tetrahydroborate; oxalyl dichloride; titanium tetrachloride; sodium hydride; dimethyl sulfoxide; (-)-sparteine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; 1.1: Swern oxidation;
DOI:10.1021/ol0615782