(R)-Methoxy-phenyl-acetic acid (3S,3aR,3bS,6aS,7aS)-3b-hydroxy-4,5-diisopropoxy-6a-methyl-6-oxo-2,3,3a,3b,6,6a,7,7a-octahydro-1H-cyclopenta[a]pentalen-3-yl ester

Base Information

• Chemical Name: (R)-Methoxy-phenyl-acetic acid (3S,3aR,3bS,6aS,7aS)-3b-hydroxy-4,5-diisopropoxy-6a-methyl-6-oxo-2,3,3a,3b,6,6a,7,7a-octahydro-1H-cyclopenta[a]pentalen-3-yl ester
• CAS No.: 188752-16-1
• Molecular Formula: C₂₇H₃₆O₇
• Molecular Weight: 472.579
• Mol file: 188752-16-1.mol

Synonyms:(R)-Methoxy-phenyl-acetic acid (3S,3aR,3bS,6aS,7aS)-3b-hydroxy-4,5-diisopropoxy-6a-methyl-6-oxo-2,3,3a,3b,6,6a,7,7a-octahydro-1H-cyclopenta[a]pentalen-3-yl ester

Chemical Property of (R)-Methoxy-phenyl-acetic acid (3S,3aR,3bS,6aS,7aS)-3b-hydroxy-4,5-diisopropoxy-6a-methyl-6-oxo-2,3,3a,3b,6,6a,7,7a-octahydro-1H-cyclopenta[a]pentalen-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-Methoxy-phenyl-acetic acid (3S,3aR,3bS,6aS,7aS)-3b-hydroxy-4,5-diisopropoxy-6a-methyl-6-oxo-2,3,3a,3b,6,6a,7,7a-octahydro-1H-cyclopenta[a]pentalen-3-yl ester

There total 5 articles about (R)-Methoxy-phenyl-acetic acid (3S,3aR,3bS,6aS,7aS)-3b-hydroxy-4,5-diisopropoxy-6a-methyl-6-oxo-2,3,3a,3b,6,6a,7,7a-octahydro-1H-cyclopenta[a]pentalen-3-yl ester 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%

(R)-(-)-α-methoxyphenylacetyl chloride (34713-98-9) + (3aS,3bR,4S,6aS,7aS)-3a,4-Dihydroxy-2,3-diisopropoxy-7a-methyl-3a,3b,4,5,6,6a,7,7a-octahydro-cyclopenta[a]pentalen-1-one (188752-15-0) → (R)-Methoxy-phenyl-acetic acid (3aS,3bR,4S,6aS,7aS)-4-hydroxy-2,3-diisopropoxy-7a-methyl-1-oxo-1,3b,4,5,6,6a,7,7a-octahydro-cyclopenta[a]pentalen-3a-yl ester + (R)-Methoxy-phenyl-acetic acid (3S,3aR,3bS,6aS,7aS)-3b-hydroxy-4,5-diisopropoxy-6a-methyl-6-oxo-2,3,3a,3b,6,6a,7,7a-octahydro-1H-cyclopenta[a]pentalen-3-yl ester (188752-16-1)

Guidance literature:

With dmap; triethylamine; In dichloromethane; for 2h;

DOI:10.1021/ja964140d

Reference yield:

(R)-methoxyphenylacetic acid (3966-32-3) → (R)-Methoxy-phenyl-acetic acid (3S,3aR,3bS,6aS,7aS)-3b-hydroxy-4,5-diisopropoxy-6a-methyl-6-oxo-2,3,3a,3b,6,6a,7,7a-octahydro-1H-cyclopenta[a]pentalen-3-yl ester (188752-16-1)

Guidance literature:

Multi-step reaction with 2 steps

1: oxalyl chloride / CH₂Cl₂ / 0 - 20 °C

2: 48 percent / triethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h

With dmap; oxalyl dichloride; triethylamine; In dichloromethane;

DOI:10.1021/ja964140d

Reference yield:

(3aS,3bS,6aS,7aS)-3a-Hydroxy-2,3-diisopropoxy-7a-methyl-3b,5,6,6a,7,7a-hexahydro-3aH-cyclopenta[a]pentalene-1,4-dione (188752-14-9) → (R)-Methoxy-phenyl-acetic acid (3S,3aR,3bS,6aS,7aS)-3b-hydroxy-4,5-diisopropoxy-6a-methyl-6-oxo-2,3,3a,3b,6,6a,7,7a-octahydro-1H-cyclopenta[a]pentalen-3-yl ester (188752-16-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / sodium borohydride / methanol

2: 48 percent / triethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h

With dmap; sodium tetrahydroborate; triethylamine; In methanol; dichloromethane;

DOI:10.1021/ja964140d

upstream raw materials:

(R)-(-)-α-methoxyphenylacetyl chloride

(3aS,3bR,4S,6aS,7aS)-3a,4-Dihydroxy-2,3-diisopropoxy-7a-methyl-3a,3b,4,5,6,6a,7,7a-octahydro-cyclopenta[a]pentalen-1-one

(R)-methoxyphenylacetic acid

(3aS,3bS,6aS,7aS)-3a-Hydroxy-2,3-diisopropoxy-7a-methyl-3b,5,6,6a,7,7a-hexahydro-3aH-cyclopenta[a]pentalene-1,4-dione