(4R)-3-[(2R,3S)-1-oxo-2-[(R)-1-(benzyloxymethyl)propyl-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)propyl-1-oxy]-3-hydroxy-5-hexenyl]-4-benzyl-1,3-oxazolidinone
CAS No.:441018-67-3
Molecular Formula:C₂₇H₃₃NO₆
Molecular Weight:467.562
Hs Code.:

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

There total 5 articles about (4R)-3-[(2R,3S)-1-oxo-2-[(R)-1-(benzyloxymethyl)propyl-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: 58.0%

: 7319-38-2
3-butenal

: 441018-65-1
(4R)-3-[1-oxo-2-[(R)-1-(benzyloxymethyl)propyl-1-oxy]ethyl]-4-benzyl-1,3-oxazolidinone

: 441018-67-3
(4R)-3-[(2R,3S)-1-oxo-2-[(R)-1-(benzyloxymethyl)propyl-1-oxy]-3-hydroxy-5-hexenyl]-4-benzyl-1,3-oxazolidinone

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

3-butenal; In dichloromethane; at -78 ℃; for 1.5h;
DOI:10.1016/S0040-4020(02)00040-6

Reference yield:

: 14618-80-5
(R)-benzyl glycidol

: 441018-67-3
(4R)-3-[(2R,3S)-1-oxo-2-[(R)-1-(benzyloxymethyl)propyl-1-oxy]-3-hydroxy-5-hexenyl]-4-benzyl-1,3-oxazolidinone

Guidance literature:: Multi-step reaction with 5 steps

1.1: 100 percent / CuI / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C

2.1: NaH / tetrahydrofuran / 0.5 h / 0 - 25 °C

2.2: 85 percent / NaH / tetrahydrofuran / 3 h / 25 °C

3.1: Et₃N / diethyl ether / -78 - 0 °C

4.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

4.2: 21.6 g / tetrahydrofuran; diethyl ether; hexane / 1.25 h / -78 - 0 °C

5.1: TiCl₄; diisopropylethylamine / CH₂Cl₂ / 2 h / -78 °C

5.2: 58 percent / CH₂Cl₂ / 1.5 h / -78 °C

With copper(l) iodide; n-butyllithium; titanium tetrachloride; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;
DOI:10.1016/S0040-4020(02)00040-6

Reference yield:

: 167354-12-3,128821-01-2
(2R)-1-(benzyloxy)-2-butanol

: 441018-67-3
(4R)-3-[(2R,3S)-1-oxo-2-[(R)-1-(benzyloxymethyl)propyl-1-oxy]-3-hydroxy-5-hexenyl]-4-benzyl-1,3-oxazolidinone

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaH / tetrahydrofuran / 0.5 h / 0 - 25 °C

1.2: 85 percent / NaH / tetrahydrofuran / 3 h / 25 °C

2.1: Et₃N / diethyl ether / -78 - 0 °C

3.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

3.2: 21.6 g / tetrahydrofuran; diethyl ether; hexane / 1.25 h / -78 - 0 °C

4.1: TiCl₄; diisopropylethylamine / CH₂Cl₂ / 2 h / -78 °C

4.2: 58 percent / CH₂Cl₂ / 1.5 h / -78 °C

With n-butyllithium; titanium tetrachloride; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;
DOI:10.1016/S0040-4020(02)00040-6