(1S,3S,3aR,6S)-7-Benzyloxy-8-methoxy-3,6,9-trimethyl-1-(2-methyl-propenyl)-2,3,3a,4,5,6-hexahydro-1H-phenalene

Base Information

• Chemical Name: (1S,3S,3aR,6S)-7-Benzyloxy-8-methoxy-3,6,9-trimethyl-1-(2-methyl-propenyl)-2,3,3a,4,5,6-hexahydro-1H-phenalene
• CAS No.: 290293-83-3
• Molecular Formula: C₂₈H₃₆O₂
• Molecular Weight: 404.593

Synonyms:(1S,3S,3aR,6S)-7-Benzyloxy-8-methoxy-3,6,9-trimethyl-1-(2-methyl-propenyl)-2,3,3a,4,5,6-hexahydro-1H-phenalene

Chemical Property of (1S,3S,3aR,6S)-7-Benzyloxy-8-methoxy-3,6,9-trimethyl-1-(2-methyl-propenyl)-2,3,3a,4,5,6-hexahydro-1H-phenalene

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Technology Process of (1S,3S,3aR,6S)-7-Benzyloxy-8-methoxy-3,6,9-trimethyl-1-(2-methyl-propenyl)-2,3,3a,4,5,6-hexahydro-1H-phenalene

There total 2 articles about (1S,3S,3aR,6S)-7-Benzyloxy-8-methoxy-3,6,9-trimethyl-1-(2-methyl-propenyl)-2,3,3a,4,5,6-hexahydro-1H-phenalene 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: 87.0%

(6S,6aR,9S)-1-Benzyloxy-3,6,9-trimethyl-4-(2-methyl-propenyl)-5,6,6a,7,8,9-hexahydro-4H-phenalen-2-ol + methyl iodide (74-88-4) → (1S,3S,3aR,6S)-7-Benzyloxy-8-methoxy-3,6,9-trimethyl-1-(2-methyl-propenyl)-2,3,3a,4,5,6-hexahydro-1H-phenalene (290293-83-3)

Guidance literature:

With potassium hydroxide; tetrabutylammomium bromide; In tetrahydrofuran; at 23 ℃; for 1h;

DOI:10.1021/ol006192k

Reference yield:

[1-benzyloxy-3,6,9-trimethyl-4-(2-methyl-propenyl)-5,6,6a,7,8,9-hexahydro-4H-phenalen-2-yloxy]-tert-butyl-dimethyl-silane → (1S,3S,3aR,6S)-7-Benzyloxy-8-methoxy-3,6,9-trimethyl-1-(2-methyl-propenyl)-2,3,3a,4,5,6-hexahydro-1H-phenalene (290293-83-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.08 h / 23 °C

2: 87 percent / potassium hydroxide; tetrabutylammonium bromide / tetrahydrofuran / 1 h / 23 °C

With potassium hydroxide; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; In tetrahydrofuran; 1: Substitution / 2: Etherification;

DOI:10.1021/ol006192k

upstream raw materials:

methyl iodide

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