(4R,6R)-(+)-4-hydroxy-6-(2-phenylethyl)-tetrahydro-2H-pyran-2-one

Base Information

• Chemical Name: (4R,6R)-(+)-4-hydroxy-6-(2-phenylethyl)-tetrahydro-2H-pyran-2-one
• CAS No.: 86117-01-3
• Molecular Formula: C₁₃H₁₆O₃
• Molecular Weight: 220.268
• Mol file: 86117-01-3.mol

Synonyms:(4R,6R)-(+)-4-hydroxy-6-(2-phenylethyl)-tetrahydro-2H-pyran-2-one

Chemical Property of (4R,6R)-(+)-4-hydroxy-6-(2-phenylethyl)-tetrahydro-2H-pyran-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,6R)-(+)-4-hydroxy-6-(2-phenylethyl)-tetrahydro-2H-pyran-2-one

There total 98 articles about (4R,6R)-(+)-4-hydroxy-6-(2-phenylethyl)-tetrahydro-2H-pyran-2-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: 85.0%

ethyl (3R,5R)-3,5-dihydroxy-7-phenylheptanoate (936716-31-3) → (4R,6R)-(+)-4-hydroxy-6-(2-phenylethyl)-tetrahydro-2H-pyran-2-one (86117-01-3)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1080/00397911.2012.754470

Reference yield: 81.0%

(+)-(3R,5S)-Methyl 7-phenyl-syn-3,5-(isopropylidenedioxy)heptanoate → (4R,6R)-(+)-4-hydroxy-6-(2-phenylethyl)-tetrahydro-2H-pyran-2-one (86117-01-3)

Guidance literature:

With acetic acid; In water; 1.) 92 deg C, 2 h, 2.) r.t., 2 h;

DOI:10.1021/jo00129a018

Reference yield: 79.0%

(3S,5R)-3,5-dihydroxy-7-phenylheptanenitrile → (4R,6R)-(+)-4-hydroxy-6-(2-phenylethyl)-tetrahydro-2H-pyran-2-one (86117-01-3)

Guidance literature:

With hydrogenchloride; water; In methanol; at 50 ℃; for 12h;

DOI:10.1016/j.tetasy.2014.12.006

upstream raw materials:

(3R,5R)-3,5-Dihydroxy-7-phenyl-heptanoic acid

ethyl (5R)-5-hydroxy-3-oxo-7-phenylheptanoate

(3S,5R)-7-Phenyl-heptane-1,3,5-triol

(4S,6R)-4-(2-hydroxyethyl)-6-(2-phenylethyl)-2,2-dimethyl-1,3-dioxane

Downstream raw materials:

(4S,6R)-4-(2-hydroxyethyl)-6-(2-phenylethyl)-2,2-dimethyl-1,3-dioxane

tert-Butyl-[2-((4S,6R)-2,2-dimethyl-6-phenethyl-[1,3]dioxan-4-yl)-ethoxy]-diphenyl-silane

Refernces

• 1、 Gadakh, Sunita K.,Sudalai, Arumugam. "Co-catalyzed two-stereocentered hydrolytic kinetic resolution: Application to the synthesis of yashabushidiols A and B and the lactone unit of compactin and mevinolin". . p. 118 - 123. Retrieved 2015/02/19.
• 2、 Mineeva. "Enantioselective synthesis of (+)-(S)-7,8-dihydrokavain and (4R,6R)-4-hydroxy-6-(2-phenylethyl)tetrahydro-2H-pyran-2-one, lactone analog of compactin and mevinolin". . p. 712 - 716. Retrieved 2013/07/11.