erythro-(1R,2S,4S)-4-(1',5'-Dimethyl-2'-diphenylphosphinoyl-1'-hydroxyhex-4'-enyl)-1,2-epoxy-1-methylcyclohexane

Base Information

• Chemical Name: erythro-(1R,2S,4S)-4-(1',5'-Dimethyl-2'-diphenylphosphinoyl-1'-hydroxyhex-4'-enyl)-1,2-epoxy-1-methylcyclohexane
• CAS No.: 214333-53-6
• Molecular Formula: C₂₇H₃₅O₃P
• Molecular Weight: 438.547

Synonyms:erythro-(1R,2S,4S)-4-(1',5'-Dimethyl-2'-diphenylphosphinoyl-1'-hydroxyhex-4'-enyl)-1,2-epoxy-1-methylcyclohexane

Chemical Property of erythro-(1R,2S,4S)-4-(1',5'-Dimethyl-2'-diphenylphosphinoyl-1'-hydroxyhex-4'-enyl)-1,2-epoxy-1-methylcyclohexane

Chemical Property:

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Technology Process of erythro-(1R,2S,4S)-4-(1',5'-Dimethyl-2'-diphenylphosphinoyl-1'-hydroxyhex-4'-enyl)-1,2-epoxy-1-methylcyclohexane

There total 2 articles about erythro-(1R,2S,4S)-4-(1',5'-Dimethyl-2'-diphenylphosphinoyl-1'-hydroxyhex-4'-enyl)-1,2-epoxy-1-methylcyclohexane 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: 61.0%

(4-Methyl-3-pentenyl) diphenylphosphine oxide (86105-38-6) + (1R,2S,4S)-4-Acetyl-1,2-epoxy-1-methylcyclohexane (111613-37-7,1932365-85-9) → (E)-(1'S,3'S,4'R)(-)-2-(3',4'-epoxy-4'-methylcyclohexyl)-6-methylhepta-2,5-diene + erythro-(1R,2S,4S)-4-(1',5'-Dimethyl-2'-diphenylphosphinoyl-1'-hydroxyhex-4'-enyl)-1,2-epoxy-1-methylcyclohexane (214333-53-6)

Guidance literature:

(4-Methyl-3-pentenyl) diphenylphosphine oxide; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at 0 ℃; for 0.5h;

(1R,2S,4S)-4-Acetyl-1,2-epoxy-1-methylcyclohexane; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 3h;

DOI:10.1055/s-2000-6253

Reference yield:

(-)-limonene oxide (203719-53-3) → erythro-(1R,2S,4S)-4-(1',5'-Dimethyl-2'-diphenylphosphinoyl-1'-hydroxyhex-4'-enyl)-1,2-epoxy-1-methylcyclohexane (214333-53-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 38 percent / KMnO₄; 18-crown-6; dibenzo-18-crown-6 / CH₂Cl₂ / 10 h / 20 °C

2.1: LDA / tetrahydrofuran; hexane / 0.5 h / 0 °C

2.2: 61 percent / tetrahydrofuran; hexane / 3 h / -78 - 20 °C

With potassium permanganate; dibenzo-18-crown-6; 18-crown-6 ether; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; 1.1: Oxidation / 2.1: Metallation / 2.2: Addition;

DOI:10.1055/s-2000-6253

Reference yield: 58.0%

erythro-(1R,2S,4S)-4-(1',5'-Dimethyl-2'-diphenylphosphinoyl-1'-hydroxyhex-4'-enyl)-1,2-epoxy-1-methylcyclohexane (214333-53-6) → (Z)-(1R,2S,4S)-4-(1',5'-Dimethylhexa-1',4'-dienyl)-1,2-epoxy-1-methylcyclohexane (111613-41-3)

Guidance literature:

With potassium hydroxide; In dimethyl sulfoxide; at 20 ℃; for 0.5h;

DOI:10.1055/s-2000-6253

upstream raw materials:

(4-Methyl-3-pentenyl) diphenylphosphine oxide

(1R,2S,4S)-4-Acetyl-1,2-epoxy-1-methylcyclohexane

(-)-limonene oxide

Downstream raw materials:

(Z)-(1R,2S,4S)-4-(1',5'-Dimethylhexa-1',4'-dienyl)-1,2-epoxy-1-methylcyclohexane

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