(2R,3R,6R)-6-((Z)-Hex-3-enyl)-2-(4-methoxy-phenoxymethyl)-3-methyl-tetrahydro-pyran-4-one

Base Information

Chemical Name:(2R,3R,6R)-6-((Z)-Hex-3-enyl)-2-(4-methoxy-phenoxymethyl)-3-methyl-tetrahydro-pyran-4-one
CAS No.:779356-71-7
Molecular Formula:C₂₀H₂₈O₄
Molecular Weight:332.44
Hs Code.:

Synonyms:(2R,3R,6R)-6-((Z)-Hex-3-enyl)-2-(4-methoxy-phenoxymethyl)-3-methyl-tetrahydro-pyran-4-one

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Chemical Property of (2R,3R,6R)-6-((Z)-Hex-3-enyl)-2-(4-methoxy-phenoxymethyl)-3-methyl-tetrahydro-pyran-4-one

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Technology Process of (2R,3R,6R)-6-((Z)-Hex-3-enyl)-2-(4-methoxy-phenoxymethyl)-3-methyl-tetrahydro-pyran-4-one

There total 6 articles about (2R,3R,6R)-6-((Z)-Hex-3-enyl)-2-(4-methoxy-phenoxymethyl)-3-methyl-tetrahydro-pyran-4-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: 77.0%

: (4R,5R)-2-((Z)-Hex-3-enyl)-4-(4-methoxy-phenoxymethyl)-5-methyl-6-methylene-[1,3]dioxane

: 779356-71-7
(2R,3R,6R)-6-((Z)-Hex-3-enyl)-2-(4-methoxy-phenoxymethyl)-3-methyl-tetrahydro-pyran-4-one

Guidance literature:: With dimethylaluminum chloride; caesium carbonate; In dichloromethane; at -78 - 20 ℃; for 1.58333h;
DOI:10.1021/ol048418f

Reference yield: 77.0%

: 779356-90-0
C₂₀H₂₈O₄

: 779356-71-7
(2R,3R,6R)-6-((Z)-Hex-3-enyl)-2-(4-methoxy-phenoxymethyl)-3-methyl-tetrahydro-pyran-4-one

Guidance literature:: C₂₀H₂₈O₄; With dimethylaluminum chloride; caesium carbonate; In dichloromethane; at -78 - 20 ℃; for 1.58333h; Inert atmosphere;

With water; sodium hydrogencarbonate; In tetrahydrofuran; diethyl ether; at -78 - 20 ℃; for 1h; Inert atmosphere;
DOI:10.1016/j.tet.2009.04.003

Reference yield:

: 6728-31-0
(Z)-4-heptenal

: 779356-71-7
(2R,3R,6R)-6-((Z)-Hex-3-enyl)-2-(4-methoxy-phenoxymethyl)-3-methyl-tetrahydro-pyran-4-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: hexamethyldisilazane / CH₂Cl₂ / 18 h / 35 °C

1.2: 2,6-di-tert-butyl-4-methylpyridine; trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 0.5 h / -78 °C

1.3: 86 percent / trifluoromethanesulfonic acid / CH₂Cl₂

2.1: ethyl trimethylacetate / tetrahydrofuran / 22 h / Heating

2.2: 100 percent / celite / tetrahydrofuran; hexane / 2 h / 20 °C

3.1: 77 percent / dimethylaluminum chloride; cesium carbonate / CH₂Cl₂ / 1.58 h / -78 - 20 °C

With 2,2-dimethyl-propanoic acid ethyl ester; dimethylaluminum chloride; caesium carbonate; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; dichloromethane; 2.1: Petasis-Tebbe methylenation / 3.1: Petasis-Ferrier rearrangement;
DOI:10.1021/ol048418f