(2S,3R)-3-((3E,7E)-(2R,6S)-2,6-Dimethyl-8-phenyl-octa-3,7-dienyl)-3-methyl-oxirane-2-carbaldehyde

Base Information

Chemical Name:(2S,3R)-3-((3E,7E)-(2R,6S)-2,6-Dimethyl-8-phenyl-octa-3,7-dienyl)-3-methyl-oxirane-2-carbaldehyde
CAS No.:883898-38-2
Molecular Formula:C₂₀H₂₆O₂
Molecular Weight:298.425
Hs Code.:

Synonyms:(2S,3R)-3-((3E,7E)-(2R,6S)-2,6-Dimethyl-8-phenyl-octa-3,7-dienyl)-3-methyl-oxirane-2-carbaldehyde

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Chemical Property of (2S,3R)-3-((3E,7E)-(2R,6S)-2,6-Dimethyl-8-phenyl-octa-3,7-dienyl)-3-methyl-oxirane-2-carbaldehyde

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Technology Process of (2S,3R)-3-((3E,7E)-(2R,6S)-2,6-Dimethyl-8-phenyl-octa-3,7-dienyl)-3-methyl-oxirane-2-carbaldehyde

There total 1 articles about (2S,3R)-3-((3E,7E)-(2R,6S)-2,6-Dimethyl-8-phenyl-octa-3,7-dienyl)-3-methyl-oxirane-2-carbaldehyde 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:

: 883898-14-4
(2R,3R,5R,6E,9S,10E)-2,3-epoxy-3,5,9-trimethyl-11-phenylundeca-6,10-dien-1-ol

: 883898-38-2
(2S,3R)-3-((3E,7E)-(2R,6S)-2,6-Dimethyl-8-phenyl-octa-3,7-dienyl)-3-methyl-oxirane-2-carbaldehyde

Guidance literature:: With pyridine; Dess-Martin periodane; In dichloromethane; at 0 ℃; for 2h;
DOI:10.1021/jo0522254

Reference yield: 71.0%

: 883898-38-2
(2S,3R)-3-((3E,7E)-(2R,6S)-2,6-Dimethyl-8-phenyl-octa-3,7-dienyl)-3-methyl-oxirane-2-carbaldehyde

: 75-16-1
methylmagnesium bromide

: 883898-15-5
(2S,3R,4R,6R,7E,10S,11E)-3,4-epoxy-4,6,10-trimethyl-12-phenyldodeca-7,11-dien-2-ol

: 883898-39-3
(2R,3R,4R,6R,7E,10S,11E)-3,4-epoxy-4,6,10-trimethyl-12-phenyldodeca-7,11-dien-2-ol

Guidance literature:: In tetrahydrofuran; diethyl ether; at -78 - 20 ℃;
DOI:10.1021/jo0522254

Reference yield:

: 883898-38-2
(2S,3R)-3-((3E,7E)-(2R,6S)-2,6-Dimethyl-8-phenyl-octa-3,7-dienyl)-3-methyl-oxirane-2-carbaldehyde

: 1,5-dimethyl-3-cyclohexenol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 71 percent / tetrahydrofuran; diethyl ether / -78 - 20 °C

2.1: 97 percent / Red-Al / tetrahydrofuran; toluene / 0 °C

3.1: t-BuOK; toluenesulfonyl chloride / tetrahydrofuran / 0 - 20 °C

3.2: 14 percent / NaH / tetrahydrofuran; various solvent(s)

4.1: 88 percent / second generation Grubbs ruthenium catalyst / CH₂Cl₂ / 3 h / 20 °C

With potassium tert-butylate; p-toluenesulfonyl chloride; sodium bis(2-methoxyethoxy)aluminium dihydride; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;
DOI:10.1021/jo0522254