(2R,3R,4S,5S,6R)-4-fluoro-2,3,5-trimethyl-6-phenyltetrahydro-2H-pyran

Base Information

• Chemical Name: (2R,3R,4S,5S,6R)-4-fluoro-2,3,5-trimethyl-6-phenyltetrahydro-2H-pyran
• CAS No.: 1351354-82-9
• Molecular Formula: C₁₄H₁₉FO
• Molecular Weight: 222.303
• Mol file: 1351354-82-9.mol

Synonyms:(2R,3R,4S,5S,6R)-4-fluoro-2,3,5-trimethyl-6-phenyltetrahydro-2H-pyran

Chemical Property of (2R,3R,4S,5S,6R)-4-fluoro-2,3,5-trimethyl-6-phenyltetrahydro-2H-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S,5S,6R)-4-fluoro-2,3,5-trimethyl-6-phenyltetrahydro-2H-pyran

There total 5 articles about (2R,3R,4S,5S,6R)-4-fluoro-2,3,5-trimethyl-6-phenyltetrahydro-2H-pyran 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: 46.0%

(2R,3S,E)-tert-butyldimethyl[(3-methylhex-4-en-2-yl)oxy]silane (1351354-73-8) + benzaldehyde (100-52-7) → (2R,3R,4S,5S,6R)-4-fluoro-2,3,5-trimethyl-6-phenyltetrahydro-2H-pyran (1351354-82-9) + (2R,3S,4S,5R,6R)-2,3,5-trimethyl-6-phenyltetrahydro-2H-pyran-4-ol (1351354-81-8)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -20 ℃; for 24h; optical yield given as %de; diastereoselective reaction;

DOI:10.1021/ol202829u

Reference yield:

methyl 2R,3R-nilate (66767-61-1) → (2R,3R,4S,5S,6R)-4-fluoro-2,3,5-trimethyl-6-phenyltetrahydro-2H-pyran (1351354-82-9) + (2R,3S,4S,5R,6R)-2,3,5-trimethyl-6-phenyltetrahydro-2H-pyran-4-ol (1351354-81-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 1H-imidazole / dichloromethane / 20 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / dichloromethane; toluene / 1.5 h / -10 - 20 °C / Inert atmosphere

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

3.2: 0.5 h / -78 °C / Inert atmosphere

4.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.42 h / -78 °C / Inert atmosphere

4.2: -78 - 20 °C / Inert atmosphere

5.1: boron trifluoride diethyl etherate / dichloromethane / 24 h / -20 °C

With 1H-imidazole; oxalyl dichloride; boron trifluoride diethyl etherate; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; toluene; 5.1: Prins reaction;

DOI:10.1021/ol202829u

Reference yield:

(2R,3R)-3-<(tert-Butyl)dimethylsilyloxy>-2-methylbuttersaeure-methylester (96597-33-0,155897-72-6) → (2R,3R,4S,5S,6R)-4-fluoro-2,3,5-trimethyl-6-phenyltetrahydro-2H-pyran (1351354-82-9) + (2R,3S,4S,5R,6R)-2,3,5-trimethyl-6-phenyltetrahydro-2H-pyran-4-ol (1351354-81-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: diisobutylaluminium hydride / dichloromethane; toluene / 1.5 h / -10 - 20 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

2.2: 0.5 h / -78 °C / Inert atmosphere

3.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.42 h / -78 °C / Inert atmosphere

3.2: -78 - 20 °C / Inert atmosphere

4.1: boron trifluoride diethyl etherate / dichloromethane / 24 h / -20 °C

With oxalyl dichloride; boron trifluoride diethyl etherate; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; toluene; 4.1: Prins reaction;

DOI:10.1021/ol202829u

upstream raw materials:

(2R,3S,E)-tert-butyldimethyl[(3-methylhex-4-en-2-yl)oxy]silane

benzaldehyde

methyl 2R,3R-nilate

(2R,3R)-3-<(tert-Butyl)dimethylsilyloxy>-2-methylbuttersaeure-methylester