(5S)-5-(4-methoxybenzyloxy)-4,4-dimethylhept-6-en-1-yn-3-one

Base Information

• Chemical Name: (5S)-5-(4-methoxybenzyloxy)-4,4-dimethylhept-6-en-1-yn-3-one
• CAS No.: 1314808-97-3
• Molecular Formula: C₁₇H₂₀O₃
• Molecular Weight: 272.344
• Mol file: 1314808-97-3.mol

Synonyms:(5S)-5-(4-methoxybenzyloxy)-4,4-dimethylhept-6-en-1-yn-3-one

Chemical Property of (5S)-5-(4-methoxybenzyloxy)-4,4-dimethylhept-6-en-1-yn-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S)-5-(4-methoxybenzyloxy)-4,4-dimethylhept-6-en-1-yn-3-one

There total 1 articles about (5S)-5-(4-methoxybenzyloxy)-4,4-dimethylhept-6-en-1-yn-3-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: 92.0%

(3RS,5S)-5-(4-methoxybenzyloxy)-4,4-dimethylhept-6-en-1-yn-3-ol → (5S)-5-(4-methoxybenzyloxy)-4,4-dimethylhept-6-en-1-yn-3-one (1314808-97-3)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.tet.2011.03.113

Reference yield: 66.0%

(5S)-5-(4-methoxybenzyloxy)-4,4-dimethylhept-6-en-1-yn-3-one (1314808-97-3) + (R)-2-(tert-butyldimethylsilyloxy)-1-[(2-trimethylsilylethoxy)methoxy]-4-(trimethylsilylmethyl)pent-4-ene (470470-78-1) → (3S,11R,6E)-11-(tert-butyldimethylsilyloxy)-4,4-dimethyl-3-(4-methoxybenzyloxy)-12-(2-trimethylsilylethoxy)methoxy-9-[(E)-trimethylsilylmethylidene]dodeca-1,6-dien-5-one (1314808-98-4)

Guidance literature:

With zinc(II) iodide; In dichloromethane; at 20 ℃; for 24h; diastereoselective reaction; Inert atmosphere; Molecular sieve; Darkness;

DOI:10.1016/j.tet.2011.03.113

Reference yield:

(5S)-5-(4-methoxybenzyloxy)-4,4-dimethylhept-6-en-1-yn-3-one (1314808-97-3) → C23H32O5

Guidance literature:

Multi-step reaction with 2 steps

1: zinc(II) iodide / dichloromethane / 24 h / 20 °C / Inert atmosphere; Molecular sieve; Darkness

2: hydrogen fluoride; water / acetonitrile / 18 h / 20 °C

With hydrogen fluoride; water; zinc(II) iodide; In dichloromethane; acetonitrile; 2: oxy-Michael reaction;

DOI:10.1016/j.tet.2011.03.113

Downstream raw materials:

(2R,6S)-2-(acetoxymethyl)-6-[(4S)-3,3-dimethyl-4-(4-methoxybenzyloxy)-2-oxohex-5-enyl]-4-methylidenetetrahydropyran

(2R,6R)-2-(acetoxymethyl)-6-[(4S)-3,3-dimethyl-4-(4-methoxybenzyloxy)-2-oxohex-5-enyl]-4-methylenetetrahydropyran

(2R,6R)-6-[(4S)-3,3-dimethyl-4-(4-methoxybenzyloxy)-2-oxohex-5-enyl]-2-[(2-trimethylsilylethoxy)methoxy]-4-[(E)-trimethylsilylmethylidene]tetrahydropyran

(2R,6S)-6-[(4S)-3,3-dimethyl-4-(4-methoxybenzyloxy)-2-oxohex-5-enyl]-2-[(2-trimethylsilylethoxy)methoxy]-4-[(E)-trimethylsilylmethylidene]tetrahydropyran