(4R)-3-[(2R,3S)-1-oxo-2-[(R)-1-(benzyloxymethyl)but-3-enyl-1-oxy]-3-hydroxy-5-hexenyl]-4-benzyl-1,3-oxazolidinone

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Chemical Name:(4R)-3-[(2R,3S)-1-oxo-2-[(R)-1-(benzyloxymethyl)but-3-enyl-1-oxy]-3-hydroxy-5-hexenyl]-4-benzyl-1,3-oxazolidinone
CAS No.:284471-58-5
Molecular Formula:C₂₈H₃₃NO₆
Molecular Weight:479.573
Hs Code.:

Synonyms:(4R)-3-[(2R,3S)-1-oxo-2-[(R)-1-(benzyloxymethyl)but-3-enyl-1-oxy]-3-hydroxy-5-hexenyl]-4-benzyl-1,3-oxazolidinone

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Chemical Property of (4R)-3-[(2R,3S)-1-oxo-2-[(R)-1-(benzyloxymethyl)but-3-enyl-1-oxy]-3-hydroxy-5-hexenyl]-4-benzyl-1,3-oxazolidinone

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Technology Process of (4R)-3-[(2R,3S)-1-oxo-2-[(R)-1-(benzyloxymethyl)but-3-enyl-1-oxy]-3-hydroxy-5-hexenyl]-4-benzyl-1,3-oxazolidinone

There total 4 articles about (4R)-3-[(2R,3S)-1-oxo-2-[(R)-1-(benzyloxymethyl)but-3-enyl-1-oxy]-3-hydroxy-5-hexenyl]-4-benzyl-1,3-oxazolidinone 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: 65.0%

: 7319-38-2
3-butenal

: 284471-60-9
(4R)-3-[1-oxo-2-[(R)-1-(benzyloxymethyl)but-3-enyl-1-oxy]-ethyl]-4-benzyl-1,3-oxazolidinone

: 284471-58-5
(4R)-3-[(2R,3S)-1-oxo-2-[(R)-1-(benzyloxymethyl)but-3-enyl-1-oxy]-3-hydroxy-5-hexenyl]-4-benzyl-1,3-oxazolidinone

Guidance literature:: (4R)-3-[1-oxo-2-[(R)-1-(benzyloxymethyl)but-3-enyl-1-oxy]-ethyl]-4-benzyl-1,3-oxazolidinone; With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃; for 2.5h;

3-butenal; In dichloromethane; at -78 ℃; for 1h; Further stages.;
DOI:10.1021/ja0007197

Reference yield:

: 58931-16-1,88981-35-5,110339-28-1
(R)-1-benzyloxypent-4-en-2-ol

: 284471-58-5
(4R)-3-[(2R,3S)-1-oxo-2-[(R)-1-(benzyloxymethyl)but-3-enyl-1-oxy]-3-hydroxy-5-hexenyl]-4-benzyl-1,3-oxazolidinone

Guidance literature:: Multi-step reaction with 4 steps

1.1: 93 percent / NaH / tetrahydrofuran / 14 h / 25 °C

2.1: Et₃N / diethyl ether / 1 h / 0 °C

3.1: nBuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C

3.2: 15.3 g / tetrahydrofuran; diethyl ether; hexane / -78 - 0 °C

4.1: TiCl₄; i-Pr₂NEt / CH₂Cl₂ / 2.5 h / -78 °C

4.2: 65 percent / CH₂Cl₂ / 1 h / -78 °C

With n-butyllithium; titanium tetrachloride; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 1.1: Alkylation / 2.1: Acylation / 3.1: Metallation / 3.2: Acylation / 4.1: complexation / 4.2: aldol reaction;
DOI:10.1021/ja0007197

Reference yield:

: 239075-68-4
(R)-1-(benzyloxymethyl)but-3-enyl-1-oxyacetic acid

: 284471-58-5
(4R)-3-[(2R,3S)-1-oxo-2-[(R)-1-(benzyloxymethyl)but-3-enyl-1-oxy]-3-hydroxy-5-hexenyl]-4-benzyl-1,3-oxazolidinone

Guidance literature:: Multi-step reaction with 3 steps

1.1: Et₃N / diethyl ether / 1 h / 0 °C

2.1: nBuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C

2.2: 15.3 g / tetrahydrofuran; diethyl ether; hexane / -78 - 0 °C

3.1: TiCl₄; i-Pr₂NEt / CH₂Cl₂ / 2.5 h / -78 °C

3.2: 65 percent / CH₂Cl₂ / 1 h / -78 °C

With n-butyllithium; titanium tetrachloride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 1.1: Acylation / 2.1: Metallation / 2.2: Acylation / 3.1: complexation / 3.2: aldol reaction;
DOI:10.1021/ja0007197