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

Base Information

• Chemical Name: (2R,3R,4R,6R,7E,10S,11E)-3,4-epoxy-4,6,10-trimethyl-12-phenyldodeca-7,11-dien-2-ol
• CAS No.: 883898-39-3
• Molecular Formula: C₂₁H₃₀O₂
• Molecular Weight: 314.468

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

Chemical Property of (2R,3R,4R,6R,7E,10S,11E)-3,4-epoxy-4,6,10-trimethyl-12-phenyldodeca-7,11-dien-2-ol

Chemical Property:

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Technology Process of (2R,3R,4R,6R,7E,10S,11E)-3,4-epoxy-4,6,10-trimethyl-12-phenyldodeca-7,11-dien-2-ol

There total 2 articles about (2R,3R,4R,6R,7E,10S,11E)-3,4-epoxy-4,6,10-trimethyl-12-phenyldodeca-7,11-dien-2-ol 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: 71.0%

(2S,3R)-3-((3E,7E)-(2R,6S)-2,6-Dimethyl-8-phenyl-octa-3,7-dienyl)-3-methyl-oxirane-2-carbaldehyde (883898-38-2) + methylmagnesium bromide (75-16-1) → (2S,3R,4R,6R,7E,10S,11E)-3,4-epoxy-4,6,10-trimethyl-12-phenyldodeca-7,11-dien-2-ol (883898-15-5) + (2R,3R,4R,6R,7E,10S,11E)-3,4-epoxy-4,6,10-trimethyl-12-phenyldodeca-7,11-dien-2-ol (883898-39-3)

Guidance literature:

In tetrahydrofuran; diethyl ether; at -78 - 20 ℃;

DOI:10.1021/jo0522254

Reference yield:

(2R,3R,5R,6E,9S,10E)-2,3-epoxy-3,5,9-trimethyl-11-phenylundeca-6,10-dien-1-ol (883898-14-4) → (2R,3R,4R,6R,7E,10S,11E)-3,4-epoxy-4,6,10-trimethyl-12-phenyldodeca-7,11-dien-2-ol (883898-39-3)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine; Dess-Martin periodinane / CH₂Cl₂ / 2 h / 0 °C

2: 25 percent / tetrahydrofuran; diethyl ether / -78 - 20 °C

With pyridine; Dess-Martin periodane; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/jo0522254

Reference yield:

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

Guidance literature:

With sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; toluene; at 0 ℃;

DOI:10.1021/jo0522254

upstream raw materials:

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

methylmagnesium bromide

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

Downstream raw materials:

(2R,4R)-2-[(2R,3E,6S,7E)-2,6-dimethyl-8-phenylocta-3,7-dienyl]-2,4-dimethyloxetane

(4S,6R,7E,10S,11E)-4,6,10-trimethyl-12-phenyldodeca-1,7,11-trien-4-ol

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

(2R,4S,6R,7E,10S,11E)-4-hydroperoxy-12-phenyl-4,6,10-trimethyldodeca-7,11-dien-2-ol

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