(4S,5R)-3-acetyl-4,5-dimethyl-4-{2-[(1S,6R)-1,2,6-trimethylcyclohex-2-enyl]ethyl}-dihydrofuran-2(3H)-one

Base Information

• Chemical Name: (4S,5R)-3-acetyl-4,5-dimethyl-4-{2-[(1S,6R)-1,2,6-trimethylcyclohex-2-enyl]ethyl}-dihydrofuran-2(3H)-one
• CAS No.: 1134565-38-0
• Molecular Formula: C₁₉H₃₀O₃
• Molecular Weight: 306.445

Synonyms:(4S,5R)-3-acetyl-4,5-dimethyl-4-{2-[(1S,6R)-1,2,6-trimethylcyclohex-2-enyl]ethyl}-dihydrofuran-2(3H)-one

Chemical Property of (4S,5R)-3-acetyl-4,5-dimethyl-4-{2-[(1S,6R)-1,2,6-trimethylcyclohex-2-enyl]ethyl}-dihydrofuran-2(3H)-one

Chemical Property:

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Technology Process of (4S,5R)-3-acetyl-4,5-dimethyl-4-{2-[(1S,6R)-1,2,6-trimethylcyclohex-2-enyl]ethyl}-dihydrofuran-2(3H)-one

There total 2 articles about (4S,5R)-3-acetyl-4,5-dimethyl-4-{2-[(1S,6R)-1,2,6-trimethylcyclohex-2-enyl]ethyl}-dihydrofuran-2(3H)-one 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: 52.0%

(5R,6S)-6-(2-iodoethyl)-1,5,6-trimethylcyclohex-1-ene (1134565-40-4) + (R)-3-acetyl-4,5-dimethylfuran-2(5H)-one → (4S,5R)-3-acetyl-4,5-dimethyl-4-{2-[(1S,6R)-1,2,6-trimethylcyclohex-2-enyl]ethyl}-dihydrofuran-2(3H)-one (1134565-38-0)

Guidance literature:

(5R,6S)-6-(2-iodoethyl)-1,5,6-trimethylcyclohex-1-ene; With tert.-butyl lithium; In diethyl ether; pentane; at -78 ℃; for 0.666667h; Inert atmosphere;

With tributylphosphine; copper(l) cyanide; In diethyl ether; pentane; at -78 - -40 ℃; for 2h; Inert atmosphere;

(R)-3-acetyl-4,5-dimethylfuran-2(5H)-one; In diethyl ether; pentane; at -78 ℃; for 1h; stereoselective reaction; Inert atmosphere;

DOI:10.1002/chem.200802021

Reference yield:

(5R,6S)-6-(2-iodoethyl)-1,5,6-trimethylcyclohex-1-ene (1134565-40-4) + (R)-3-acetyl-4,5-dimethylfuran-2(5H)-one → (4S,5R)-3-acetyl-4,5-dimethyl-4-{2-[(1S,6R)-1,2,6-trimethylcyclohex-2-enyl]ethyl}-dihydrofuran-2(3H)-one (1134565-38-0) + C19H30O3

Guidance literature:

With copper(l) iodide; tert.-butyl lithium; stereoselective reaction; Inert atmosphere; Cooling;

DOI:10.1002/chem.200802021

Reference yield: 95.0%

(4S,5R)-3-acetyl-4,5-dimethyl-4-{2-[(1S,6R)-1,2,6-trimethylcyclohex-2-enyl]ethyl}-dihydrofuran-2(3H)-one (1134565-38-0) + acetic anhydride (108-24-7) → 1-[(4S,5R)-4,5-dimethyl-2-oxo-4-{2-[(1S,6R)-1,2,6-trimethylcyclohex-2-enyl]ethyl}-dihydrofuran-3(2H)-ylidene]ethyl acetate (1134565-72-2)

Guidance literature:

With pyridine; In dichloromethane; for 12h; Reflux;

DOI:10.1002/chem.200802021

upstream raw materials:

(5R,6S)-6-(2-iodoethyl)-1,5,6-trimethylcyclohex-1-ene

Downstream raw materials:

1-[(4S,5R)-4,5-dimethyl-2-oxo-4-{2-[(1S,6R)-1,2,6-trimethylcyclohex-2-enyl]ethyl}-dihydrofuran-3(2H)-ylidene]ethyl acetate

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