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

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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-oxazolidin-2-thione
CAS No.:284471-82-5
Molecular Formula:C₂₈H₃₃NO₅S
Molecular Weight:495.64
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-oxazolidin-2-thione

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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-oxazolidin-2-thione

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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-oxazolidin-2-thione

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-oxazolidin-2-thione 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: 57.0%

: 7319-38-2
3-butenal

: 284471-81-4
(4R)-3-[1-oxo-2-[(R)-1-(benzyloxymethyl)but-3-enyl-1-oxy]-ethyl]-4-benzyl-1,3-oxazolidin-2-thione

: 284471-82-5
(4R)-3-[(2R,3S)-1-oxo-2-[(R)-1-(benzyloxymethyl)but-3-enyl-1-oxy]-3-hydroxy-5-hexenyl]-4-benzyl-1,3-oxazolidin-2-thione

Guidance literature:: (4R)-3-[1-oxo-2-[(R)-1-(benzyloxymethyl)but-3-enyl-1-oxy]-ethyl]-4-benzyl-1,3-oxazolidin-2-thione; 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

: 284471-82-5
(4R)-3-[(2R,3S)-1-oxo-2-[(R)-1-(benzyloxymethyl)but-3-enyl-1-oxy]-3-hydroxy-5-hexenyl]-4-benzyl-1,3-oxazolidin-2-thione

Guidance literature:: Multi-step reaction with 4 steps

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

2.1: oxalyl chloride / DMF / CH₂Cl₂ / 2 h / 25 °C

3.1: 1.98 g / Et₃N / CH₂Cl₂ / 0 - 25 °C

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

4.2: 57 percent / CH₂Cl₂ / 1 h / -78 °C

With oxalyl dichloride; titanium tetrachloride; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; In tetrahydrofuran; dichloromethane; 1.1: Alkylation / 2.1: Substitution / 3.1: 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

: 284471-82-5
(4R)-3-[(2R,3S)-1-oxo-2-[(R)-1-(benzyloxymethyl)but-3-enyl-1-oxy]-3-hydroxy-5-hexenyl]-4-benzyl-1,3-oxazolidin-2-thione

Guidance literature:: Multi-step reaction with 3 steps

1.1: oxalyl chloride / DMF / CH₂Cl₂ / 2 h / 25 °C

2.1: 1.98 g / Et₃N / CH₂Cl₂ / 0 - 25 °C

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

3.2: 57 percent / CH₂Cl₂ / 1 h / -78 °C

With oxalyl dichloride; titanium tetrachloride; triethylamine; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; In dichloromethane; 1.1: Substitution / 2.1: Acylation / 3.1: complexation / 3.2: aldol reaction;
DOI:10.1021/ja0007197