(4S)-3-((2S)-6-[(2S,3S,5S)-5-allyl-3-methyltetrahydro-2-furanyl]-2-methylhexanoyl)-4-benzyl-1,3-oxazolan-2-one

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Chemical Name:(4S)-3-((2S)-6-[(2S,3S,5S)-5-allyl-3-methyltetrahydro-2-furanyl]-2-methylhexanoyl)-4-benzyl-1,3-oxazolan-2-one
CAS No.:1146690-90-5
Molecular Formula:C₂₅H₃₅NO₄
Molecular Weight:413.557
Hs Code.:

Synonyms:(4S)-3-((2S)-6-[(2S,3S,5S)-5-allyl-3-methyltetrahydro-2-furanyl]-2-methylhexanoyl)-4-benzyl-1,3-oxazolan-2-one

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Chemical Property of (4S)-3-((2S)-6-[(2S,3S,5S)-5-allyl-3-methyltetrahydro-2-furanyl]-2-methylhexanoyl)-4-benzyl-1,3-oxazolan-2-one

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Technology Process of (4S)-3-((2S)-6-[(2S,3S,5S)-5-allyl-3-methyltetrahydro-2-furanyl]-2-methylhexanoyl)-4-benzyl-1,3-oxazolan-2-one

There total 15 articles about (4S)-3-((2S)-6-[(2S,3S,5S)-5-allyl-3-methyltetrahydro-2-furanyl]-2-methylhexanoyl)-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: 80.0%

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

: 74-88-4
methyl iodide

: 1146690-90-5
(4S)-3-((2S)-6-[(2S,3S,5S)-5-allyl-3-methyltetrahydro-2-furanyl]-2-methylhexanoyl)-4-benzyl-1,3-oxazolan-2-one

Guidance literature:: (4S)-3-{6-[(2S,3S,5S)-5-allyl-3-methyl-tetrahydrofuran-2-yl]hexanoyl}-4-benzyl-1,3-oxazolan-2-one; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

methyl iodide; In tetrahydrofuran; at -78 ℃; for 3h; Inert atmosphere;
DOI:10.1021/ol9002724

Reference yield:

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

: 1146690-90-5
(4S)-3-((2S)-6-[(2S,3S,5S)-5-allyl-3-methyltetrahydro-2-furanyl]-2-methylhexanoyl)-4-benzyl-1,3-oxazolan-2-one

Guidance literature:: Multi-step reaction with 8 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

8.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

8.2: 3 h / -78 °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; sodium hexamethyldisilazane; pivaloyl chloride; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; water; acetone; acetonitrile; benzene; 3.1: Jones oxidation;
DOI:10.1002/ejoc.201001205

Reference yield:

: 1146690-68-7
(2S)-2-[6-(benzyloxy)hexyl]-5-ethoxy-3-methylenetetrahydrofuran

: 1146690-90-5
(4S)-3-((2S)-6-[(2S,3S,5S)-5-allyl-3-methyltetrahydro-2-furanyl]-2-methylhexanoyl)-4-benzyl-1,3-oxazolan-2-one

Guidance literature:: Multi-step reaction with 7 steps

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

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

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

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

5.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / water; acetonitrile / Inert atmosphere

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

6.2: 3 h / -20 - 0 °C / Inert atmosphere

7.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

7.2: 3 h / -78 °C / Inert atmosphere

With sodium tetrahydroborate; Jones reagent; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; nickel(II) chloride hexahydrate; [bis(acetoxy)iodo]benzene; iodine; sodium hexamethyldisilazane; pivaloyl chloride; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; water; acetone; acetonitrile; 2.1: Jones oxidation;
DOI:10.1002/ejoc.201001205