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

Base Information

• Chemical Name: (3R,5S)-5-(4-methoxybenzyloxy)-4,4-dimethylhept-6-en-1-yn-3-ol
• CAS No.: 1314808-95-1
• Molecular Formula: C₁₇H₂₂O₃
• Molecular Weight: 274.36
• Mol file: 1314808-95-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about (3R,5S)-5-(4-methoxybenzyloxy)-4,4-dimethylhept-6-en-1-yn-3-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: 48.0%

(3S)-3-[(4-methoxyphenyl)methoxy]-2,2-dimethylpent-4-enal (861118-37-8) + acetylenemagnesium bromide (4301-14-8) → (3R,5S)-5-(4-methoxybenzyloxy)-4,4-dimethylhept-6-en-1-yn-3-ol (1314808-95-1) + (3S,5S)-5-(4-methoxybenzyloxy)-4,4-dimethylhept-6-en-1-yn-3-ol (1314808-94-0)

Guidance literature:

(3S)-3-[(4-methoxyphenyl)methoxy]-2,2-dimethylpent-4-enal; acetylenemagnesium bromide; In tetrahydrofuran; at -78 - 20 ℃; for 18h; Inert atmosphere;

With ammonium chloride; In tetrahydrofuran; water;

DOI:10.1016/j.tet.2011.03.113

Reference yield:

(2RS,3R)-3-(4-methoxybenzyloxy)-4,4-dimethyltetrahydrofuran-2-ol (1224963-20-5) → (3R,5S)-5-(4-methoxybenzyloxy)-4,4-dimethylhept-6-en-1-yn-3-ol (1314808-95-1) + (3S,5S)-5-(4-methoxybenzyloxy)-4,4-dimethylhept-6-en-1-yn-3-ol (1314808-94-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran; hexanes / 0.5 h / -78 - 0 °C / Inert atmosphere

1.2: 15 h / -78 - 20 °C / Inert atmosphere

2.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 3 h / 20 °C / Inert atmosphere; Molecular sieve

3.1: tetrahydrofuran / 18 h / -78 - 20 °C / Inert atmosphere

With n-butyllithium; tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide; In tetrahydrofuran; hexanes; dichloromethane; 1.2: Wittig reaction;

DOI:10.1016/j.tet.2011.03.113

Reference yield:

(3R)-3-(4-methoxybenzyloxy)-4,4-dimethyltetrahydrofuran-2-one → (3R,5S)-5-(4-methoxybenzyloxy)-4,4-dimethylhept-6-en-1-yn-3-ol (1314808-95-1) + (3S,5S)-5-(4-methoxybenzyloxy)-4,4-dimethylhept-6-en-1-yn-3-ol (1314808-94-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: diisobutylaluminium hydride / tetrahydrofuran / 5 h / -78 - -35 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexanes / 0.5 h / -78 - 0 °C / Inert atmosphere

2.2: 15 h / -78 - 20 °C / Inert atmosphere

3.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 3 h / 20 °C / Inert atmosphere; Molecular sieve

4.1: tetrahydrofuran / 18 h / -78 - 20 °C / Inert atmosphere

With n-butyllithium; tetrapropylammonium perruthennate; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; hexanes; dichloromethane; 2.2: Wittig reaction;

DOI:10.1016/j.tet.2011.03.113

upstream raw materials:

(3S)-3-[(4-methoxyphenyl)methoxy]-2,2-dimethylpent-4-enal

acetylenemagnesium bromide

(2RS,3R)-3-(4-methoxybenzyloxy)-4,4-dimethyltetrahydrofuran-2-ol