(S)-methyl mandelyl tetrahydropyranyl ether

Base Information

• Chemical Name: (S)-methyl mandelyl tetrahydropyranyl ether
• CAS No.: 128854-82-0
• Molecular Formula: C₁₄H₁₈O₄
• Molecular Weight: 250.295
• Mol file: 128854-82-0.mol

Synonyms:(S)-methyl mandelyl tetrahydropyranyl ether

Chemical Property of (S)-methyl mandelyl tetrahydropyranyl ether

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-methyl mandelyl tetrahydropyranyl ether

There total 5 articles about (S)-methyl mandelyl tetrahydropyranyl ether 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: 100.0%

3,4-dihydro-2H-pyran (110-87-2) + (R)-methyl mandelate (20698-91-3) → R-(-)-methyl 2-phenyl-2-(tetrahydropyranyloxy)acetate (33973-12-5,128854-60-4,128854-82-0,133867-57-9)

Guidance literature:

pyridinium p-toluenesulfonate; In dichloromethane; 10 min at 0 deg C and 2 h at r.t.;

DOI:10.1021/jo00010a028

Reference yield: 42.0%

3,4-dihydro-2H-pyran (110-87-2) + (S)-Methyl mandelate (21210-43-5) → (S)-methyl mandelyl tetrahydropyranyl ether (128854-82-0) + (S)-methyl mandelyl tetrahydropyranyl ether (128854-60-4)

Guidance literature:

DOI:10.1016/S0040-4039(01)93919-X

Reference yield:

(R)-Mandelic Acid (611-71-2) → R-(-)-methyl 2-phenyl-2-(tetrahydropyranyloxy)acetate (33973-12-5,128854-60-4,128854-82-0,133867-57-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / SOCl₂ / 10 min at -10 deg C and 4 h at r.t.

2: 100 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 10 min at 0 deg C and 2 h at r.t.

With thionyl chloride; pyridinium p-toluenesulfonate; In dichloromethane;

DOI:10.1021/jo00010a028

upstream raw materials:

3,4-dihydro-2H-pyran

(S)-Methyl mandelate

(R)-methyl mandelate

(R)-Mandelic Acid

Downstream raw materials:

(R,R)-(-)-1,11-diphenyl-3,6,9-trioxaundecane-1,11-diol

(4R,14R)-(-)-4,14-diphenyl-3,6,9,12,15-pentaoxa-21-azabicyclo<15.3.1>heneicosa-1(21),17,19-triene

(R)-(+)-2-chloro-2-phenylethyl p-chlorophenyl sulfone

(R)-(+)-2-chloro-2-phenylethyl p-tolyl sulfone

Refernces

• 1、 Huszthy, Peter,Bradshaw, Jerald S.,Zhu, Cheng Y.,Izatt, Reed M.,Lifson, Shneior. "Recognition by New Symmetrically Substituted Chiral Diphenyl- and Di-tert-butylpyridino-18-crown-6 and Asymmetrically Substituted Chiral Dimethylpyridino-18-crown-6 Ligands of the Enantiomers of Various Organic Ammonium Perchlorates". . p. 3330 - 3336. Retrieved 2007/10/02.
• 2、 Kameyama, Masayuki,Kamigata, Nobumasa,Kobayashi, Michio. "Asymmetric Radical Reaction in the Coordination Sphere. 2. Asymmetric Addition of Alkane- and Arenesulfonyl Chlorides to Olefins Catalyzed by a Ruthenium(II)-Phosphine Complex with Chiral Ligands". . p. 3312 - 3316. Retrieved 2007/10/02.