(4S,5R,6R)-4-allyl-6-((2R,Z)-6-((4-methoxybenzyl)oxy)hex-4-en-2-yl)-2,2,5-trimethyl-1,3-dioxane

Base Information

Chemical Name:(4S,5R,6R)-4-allyl-6-((2R,Z)-6-((4-methoxybenzyl)oxy)hex-4-en-2-yl)-2,2,5-trimethyl-1,3-dioxane
CAS No.:1415635-84-5
Molecular Formula:C₂₄H₃₆O₄
Molecular Weight:388.547
Hs Code.:

Synonyms:(4S,5R,6R)-4-allyl-6-((2R,Z)-6-((4-methoxybenzyl)oxy)hex-4-en-2-yl)-2,2,5-trimethyl-1,3-dioxane

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Chemical Property of (4S,5R,6R)-4-allyl-6-((2R,Z)-6-((4-methoxybenzyl)oxy)hex-4-en-2-yl)-2,2,5-trimethyl-1,3-dioxane

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Technology Process of (4S,5R,6R)-4-allyl-6-((2R,Z)-6-((4-methoxybenzyl)oxy)hex-4-en-2-yl)-2,2,5-trimethyl-1,3-dioxane

There total 10 articles about (4S,5R,6R)-4-allyl-6-((2R,Z)-6-((4-methoxybenzyl)oxy)hex-4-en-2-yl)-2,2,5-trimethyl-1,3-dioxane 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:

: 1415635-91-4
C₂₁H₃₂O₄

: 77-76-9
2,2-dimethoxy-propane

: 1415635-84-5
(4S,5R,6R)-4-allyl-6-((2R,Z)-6-((4-methoxybenzyl)oxy)hex-4-en-2-yl)-2,2,5-trimethyl-1,3-dioxane

Guidance literature:: With pyridinium p-toluenesulfonate; In acetone; at 20 ℃; for 2h; Inert atmosphere;
DOI:10.1021/ol302999v

Reference yield:

: 1415635-78-7
(R,Z)-N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-6-((4-methoxybenzyl)oxy)-N,2-dimethylhex-4-enamide

: 1415635-84-5
(4S,5R,6R)-4-allyl-6-((2R,Z)-6-((4-methoxybenzyl)oxy)hex-4-en-2-yl)-2,2,5-trimethyl-1,3-dioxane

Guidance literature:: Multi-step reaction with 9 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran; hexane; ethyl acetate / 1 h / -78 - 0 °C / Inert atmosphere

2.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 2.67 h / -78 - 20 °C / Inert atmosphere

2.2: 3 h / -78 °C / Inert atmosphere

2.3: 3 h / -116 °C / Inert atmosphere

3.1: tetra(n-butyl)ammonium hydroxide / tert-butyl alcohol; water / 20 h / 50 °C / Inert atmosphere

4.1: N-ethyl-N,N-diisopropylamine; 1-[(1-(cyano-?2-?ethoxy-?2-?oxoethylidenaminooxy)?dimethylamino-?morpholino)]-uronium hexafluorophosphate / N,N-dimethyl-formamide / 0.75 h / 20 °C / Inert atmosphere

4.2: 1 h / Inert atmosphere

5.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

6.1: diisobutylaluminium hydride / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

7.1: diethyl ether / 3 h / -78 °C / Inert atmosphere

7.2: 4 h / Inert atmosphere; Reflux

8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

9.1: pyridinium p-toluenesulfonate / acetone / 2 h / 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; n-butyllithium; 1-[(1-(cyano-?2-?ethoxy-?2-?oxoethylidenaminooxy)?dimethylamino-?morpholino)]-uronium hexafluorophosphate; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydroxide; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; diisopropylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;
DOI:10.1021/ol302999v

Reference yield:

: 1385018-40-5
(R,Z)-6-((4-methoxybenzyl)oxy)-2-methylhex-4-enal

: 1415635-84-5
(4S,5R,6R)-4-allyl-6-((2R,Z)-6-((4-methoxybenzyl)oxy)hex-4-en-2-yl)-2,2,5-trimethyl-1,3-dioxane

Guidance literature:: Multi-step reaction with 8 steps

1.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 2.67 h / -78 - 20 °C / Inert atmosphere

1.2: 3 h / -78 °C / Inert atmosphere

1.3: 3 h / -116 °C / Inert atmosphere

2.1: tetra(n-butyl)ammonium hydroxide / tert-butyl alcohol; water / 20 h / 50 °C / Inert atmosphere

3.1: N-ethyl-N,N-diisopropylamine; 1-[(1-(cyano-?2-?ethoxy-?2-?oxoethylidenaminooxy)?dimethylamino-?morpholino)]-uronium hexafluorophosphate / N,N-dimethyl-formamide / 0.75 h / 20 °C / Inert atmosphere

3.2: 1 h / Inert atmosphere

4.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

5.1: diisobutylaluminium hydride / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

6.1: diethyl ether / 3 h / -78 °C / Inert atmosphere

6.2: 4 h / Inert atmosphere; Reflux

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

8.1: pyridinium p-toluenesulfonate / acetone / 2 h / 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; n-butyllithium; 1-[(1-(cyano-?2-?ethoxy-?2-?oxoethylidenaminooxy)?dimethylamino-?morpholino)]-uronium hexafluorophosphate; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydroxide; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; diisopropylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;
DOI:10.1021/ol302999v