(2R,3S,4R,5R,6R)-2-((Z)-Hex-3-enyl)-6-(4-methoxy-phenoxymethyl)-5-methyl-tetrahydro-pyran-3,4-diol

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Chemical Name:(2R,3S,4R,5R,6R)-2-((Z)-Hex-3-enyl)-6-(4-methoxy-phenoxymethyl)-5-methyl-tetrahydro-pyran-3,4-diol
CAS No.:779356-73-9
Molecular Formula:C₂₀H₃₀O₅
Molecular Weight:350.455
Hs Code.:

Synonyms:(2R,3S,4R,5R,6R)-2-((Z)-Hex-3-enyl)-6-(4-methoxy-phenoxymethyl)-5-methyl-tetrahydro-pyran-3,4-diol

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Chemical Property of (2R,3S,4R,5R,6R)-2-((Z)-Hex-3-enyl)-6-(4-methoxy-phenoxymethyl)-5-methyl-tetrahydro-pyran-3,4-diol

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Technology Process of (2R,3S,4R,5R,6R)-2-((Z)-Hex-3-enyl)-6-(4-methoxy-phenoxymethyl)-5-methyl-tetrahydro-pyran-3,4-diol

There total 9 articles about (2R,3S,4R,5R,6R)-2-((Z)-Hex-3-enyl)-6-(4-methoxy-phenoxymethyl)-5-methyl-tetrahydro-pyran-3,4-diol 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%

: 779356-72-8
(2R,3R,5S,6R)-2-((Z)-Hex-3-enyl)-3-hydroxy-6-(4-methoxy-phenoxymethyl)-5-methyl-tetrahydro-pyran-4-one

: (2R,3S,4S,5R,6R)-2-((Z)-Hex-3-enyl)-6-(4-methoxy-phenoxymethyl)-5-methyl-tetrahydro-pyran-3,4-diol

: 779356-73-9
(2R,3S,4R,5R,6R)-2-((Z)-Hex-3-enyl)-6-(4-methoxy-phenoxymethyl)-5-methyl-tetrahydro-pyran-3,4-diol

Guidance literature:: (2R,3R,5S,6R)-2-((Z)-Hex-3-enyl)-3-hydroxy-6-(4-methoxy-phenoxymethyl)-5-methyl-tetrahydro-pyran-4-one; With 1H-imidazole; dmap; chloro-trimethyl-silane; In dichloromethane; at 20 ℃; for 24h;

With tetrabutylammonium borohydride; In dichloromethane; at -78 - -40 ℃; for 3.5h;
DOI:10.1021/ol048418f

Reference yield:

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

: 779356-73-9
(2R,3S,4R,5R,6R)-2-((Z)-Hex-3-enyl)-6-(4-methoxy-phenoxymethyl)-5-methyl-tetrahydro-pyran-3,4-diol

Guidance literature:: Multi-step reaction with 6 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

4.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / -78 °C

4.2: 78 percent / (1S)-3,3-dimethoxy-(10-camphorsulfonyl)oxaziridine; hexamethylphosphoramide / tetrahydrofuran; CH₂Cl₂ / 2 h / -60 °C

5.1: 4.32 g / K₂CO₃ / methanol / 1 h

6.1: chlorotrimethylsilane; 4-dimethylaminopyridine; imidazole / CH₂Cl₂ / 24 h / 20 °C

6.2: 85 percent / tetrabutylammonium borohydride / CH₂Cl₂ / 3.5 h / -78 - -40 °C

With 1H-imidazole; dmap; chloro-trimethyl-silane; 2,2-dimethyl-propanoic acid ethyl ester; dimethylaluminum chloride; potassium hexamethylsilazane; potassium carbonate; caesium carbonate; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; methanol; dichloromethane; 2.1: Petasis-Tebbe methylenation / 3.1: Petasis-Ferrier rearrangement;
DOI:10.1021/ol048418f

Reference yield:

: 68426-09-5
(4-methoxyphenoxy)acetaldehyde

: 779356-73-9
(2R,3S,4R,5R,6R)-2-((Z)-Hex-3-enyl)-6-(4-methoxy-phenoxymethyl)-5-methyl-tetrahydro-pyran-3,4-diol

Guidance literature:: Multi-step reaction with 7 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

4.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / -78 °C

4.2: 78 percent / (1S)-3,3-dimethoxy-(10-camphorsulfonyl)oxaziridine; hexamethylphosphoramide / tetrahydrofuran; CH₂Cl₂ / 2 h / -60 °C

5.1: 4.32 g / K₂CO₃ / methanol / 1 h

6.1: chlorotrimethylsilane; 4-dimethylaminopyridine; imidazole / CH₂Cl₂ / 24 h / 20 °C

6.2: 85 percent / tetrabutylammonium borohydride / CH₂Cl₂ / 3.5 h / -78 - -40 °C

With 1H-imidazole; dmap; chloro-trimethyl-silane; 2,2-dimethyl-propanoic acid ethyl ester; dimethylaluminum chloride; potassium hexamethylsilazane; potassium carbonate; caesium carbonate; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; methanol; dichloromethane; 3.1: Petasis-Tebbe methylenation / 4.1: Petasis-Ferrier rearrangement;
DOI:10.1021/ol048418f