(4S)-3-{6-[(2S,3S,5S)-5-allyl-3-methyl-tetrahydrofuran-2-yl]hexanoyl}-4-benzyl-1,3-oxazolan-2-one

Base Information

Chemical Name:(4S)-3-{6-[(2S,3S,5S)-5-allyl-3-methyl-tetrahydrofuran-2-yl]hexanoyl}-4-benzyl-1,3-oxazolan-2-one
CAS No.:1146690-75-6
Molecular Formula:C₂₄H₃₃NO₄
Molecular Weight:399.53
Hs Code.:

Synonyms:(4S)-3-{6-[(2S,3S,5S)-5-allyl-3-methyl-tetrahydrofuran-2-yl]hexanoyl}-4-benzyl-1,3-oxazolan-2-one

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Chemical Property of (4S)-3-{6-[(2S,3S,5S)-5-allyl-3-methyl-tetrahydrofuran-2-yl]hexanoyl}-4-benzyl-1,3-oxazolan-2-one

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Technology Process of (4S)-3-{6-[(2S,3S,5S)-5-allyl-3-methyl-tetrahydrofuran-2-yl]hexanoyl}-4-benzyl-1,3-oxazolan-2-one

There total 15 articles about (4S)-3-{6-[(2S,3S,5S)-5-allyl-3-methyl-tetrahydrofuran-2-yl]hexanoyl}-4-benzyl-1,3-oxazolan-2-one 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: 85.0%

: 1146690-89-2
6-[(2S,3S,5S)-5-allyl-3-methyltetrahydro-2-furanyl]hexanoic acid

: 90719-32-7
(S)-4-Benzyl-2-oxazolidinone

: 1146690-75-6
(4S)-3-{6-[(2S,3S,5S)-5-allyl-3-methyl-tetrahydrofuran-2-yl]hexanoyl}-4-benzyl-1,3-oxazolan-2-one

Guidance literature:: 6-[(2S,3S,5S)-5-allyl-3-methyltetrahydro-2-furanyl]hexanoic acid; With pivaloyl chloride; triethylamine; In tetrahydrofuran; at -20 ℃; for 1h; Inert atmosphere;

(S)-4-Benzyl-2-oxazolidinone; With lithium chloride; In tetrahydrofuran; at -20 - 0 ℃; for 3h; Inert atmosphere;
DOI:10.1002/ejoc.201001205

Reference yield:

: C₁₉H₃₂O₄

: 90719-32-7
(S)-4-Benzyl-2-oxazolidinone

: 1146690-75-6
(4S)-3-{6-[(2S,3S,5S)-5-allyl-3-methyl-tetrahydrofuran-2-yl]hexanoyl}-4-benzyl-1,3-oxazolan-2-one

Guidance literature:: With lithium chloride; at -20 - 0 ℃; for 3h;
DOI:10.1021/ol9002724

Reference yield:

: 1146690-87-0
(3S)-9-(benzyloxy)-3-(2-bromo-1-ethoxyethoxy)-1-nonyne

: 1146690-75-6
(4S)-3-{6-[(2S,3S,5S)-5-allyl-3-methyl-tetrahydrofuran-2-yl]hexanoyl}-4-benzyl-1,3-oxazolan-2-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / benzene / 0.5 h / Inert atmosphere; Reflux

2.1: sodium tetrahydroborate; nickel(II) chloride hexahydrate / methanol / 1 h / 0 - 20 °C / Inert atmosphere

3.1: Jones reagent / acetone / 0 - 20 °C / Inert atmosphere

4.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -78 °C / Inert atmosphere

5.1: iodine / dichloromethane / -78 - 20 °C / Inert atmosphere

6.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / water; acetonitrile / Inert atmosphere

7.1: pivaloyl chloride; triethylamine / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere

7.2: 3 h / -20 - 0 °C / Inert atmosphere

With sodium tetrahydroborate; Jones reagent; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; nickel(II) chloride hexahydrate; 2,2'-azobis(isobutyronitrile); [bis(acetoxy)iodo]benzene; iodine; tri-n-butyl-tin hydride; pivaloyl chloride; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; water; acetone; acetonitrile; benzene; 3.1: Jones oxidation;
DOI:10.1002/ejoc.201001205