(R)-O-methylmandelic acid ester of methyl (+)-(1R,2R,3S,5S)-3-hydroxy-7,7-(ethylenedioxy)bicyclo<3.3.0>octane-2-carboxylate

Base Information

• Chemical Name: (R)-O-methylmandelic acid ester of methyl (+)-(1R,2R,3S,5S)-3-hydroxy-7,7-(ethylenedioxy)bicyclo<3.3.0>octane-2-carboxylate
• CAS No.: 108168-31-6
• Molecular Formula: C₂₁H₂₆O₇
• Molecular Weight: 390.433
• Mol file: 108168-31-6.mol

Synonyms:

Chemical Property of (R)-O-methylmandelic acid ester of methyl (+)-(1R,2R,3S,5S)-3-hydroxy-7,7-(ethylenedioxy)bicyclo<3.3.0>octane-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-O-methylmandelic acid ester of methyl (+)-(1R,2R,3S,5S)-3-hydroxy-7,7-(ethylenedioxy)bicyclo<3.3.0>octane-2-carboxylate

There total 2 articles about (R)-O-methylmandelic acid ester of methyl (+)-(1R,2R,3S,5S)-3-hydroxy-7,7-(ethylenedioxy)bicyclo<3.3.0>octane-2-carboxylate 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:

methyl (+/-)-3-oxo-7,7-(ethylenedioxy)bicyclo<3.3.0>octane-2-carboxylate (69552-47-2,71773-24-5,82863-52-3,89888-63-1,122292-76-6,130549-62-1,130549-63-2) → (R)-O-methylmandelic acid ester of methyl (+)-(1R,2R,3S,5S)-3-hydroxy-7,7-(ethylenedioxy)bicyclo<3.3.0>octane-2-carboxylate (108168-31-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 43 percent / H₂O / 48 h / 25 °C / pH₇ phosphate buffer, D-glucose, yeast extract, active bakers' yeast

2: 1.) oxalyl chloride, DMF, 2.) pyridine / 1.) acetonitrile, 0 deg C, 10 min 2.) acetonitrile, 0 deg C, 1 h

With pyridine; oxalyl dichloride; N,N-dimethyl-formamide; In water;

DOI:10.1021/jo00387a026

Reference yield:

(R)-methoxyphenylacetic acid (3966-32-3) + methyl (+)-(1R,2R,3S,5S)-3-hydroxy-7,7-(ethylenedioxy)bicyclo<3.3.0>octane-2-carboxylate (105499-51-2) → (R)-O-methylmandelic acid ester of methyl (+)-(1R,2R,3S,5S)-3-hydroxy-7,7-(ethylenedioxy)bicyclo<3.3.0>octane-2-carboxylate (108168-31-6)

Guidance literature:

With pyridine; oxalyl dichloride; N,N-dimethyl-formamide; Yield given. Multistep reaction; 1.) acetonitrile, 0 deg C, 10 min 2.) acetonitrile, 0 deg C, 1 h;

DOI:10.1021/jo00387a026

Reference yield:

(R)-O-methylmandelic acid ester of methyl (+)-(1R,2R,3S,5S)-3-hydroxy-7,7-(ethylenedioxy)bicyclo<3.3.0>octane-2-carboxylate (108168-31-6) → (R)-O-Methylmandelic acid ester of methyl (+)-(1R,2R,3S,5S)-3-hydroxy-7-oxobicyclo<3.3.0>octane-2-carboxylate (108168-32-7)

Guidance literature:

With hydrogenchloride;

DOI:10.1021/jo00387a026

upstream raw materials:

(R)-methoxyphenylacetic acid

methyl (+)-(1R,2R,3S,5S)-3-hydroxy-7,7-(ethylenedioxy)bicyclo<3.3.0>octane-2-carboxylate

methyl (+/-)-3-oxo-7,7-(ethylenedioxy)bicyclo<3.3.0>octane-2-carboxylate

Downstream raw materials:

(R)-O-Methylmandelic acid ester of methyl (+)-(1R,2R,3S,5S)-3-hydroxy-7-oxobicyclo<3.3.0>octane-2-carboxylate