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

Base Information

• Chemical Name: methyl (+)-(1R,2R,3S,5S)-3-hydroxy-7,7-(ethylenedioxy)bicyclo<3.3.0>octane-2-carboxylate
• CAS No.: 105499-51-2
• Molecular Formula: C₁₂H₁₈O₅
• Molecular Weight: 242.272
• Mol file: 105499-51-2.mol

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

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

There total 1 articles about 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: 43.0%

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) → 7,7-ethylenedioxy-3-oxo-cis-bicyclo[3.3.0]octane (51716-62-2) + methyl (+)-(1R,2R,3S,5S)-3-hydroxy-7,7-(ethylenedioxy)bicyclo<3.3.0>octane-2-carboxylate (105499-51-2)

Guidance literature:

In water; at 25 ℃; for 48h; pH₇ phosphate buffer, D-glucose, yeast extract, active bakers' yeast;

DOI:10.1021/jo00387a026

Reference yield: 98.0%

(S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride (39637-99-5,20445-33-4) + methyl (+)-(1R,2R,3S,5S)-3-hydroxy-7,7-(ethylenedioxy)bicyclo<3.3.0>octane-2-carboxylate (105499-51-2) → (S)-α-methoxy-α-(trifluoromethyl)pnenylacetyl acid ester of methyl (+)-(1R,2R,3S,5S)-3-hydroxy-7,7-(ethylenedioxy)bicyclo<3.3.0>octane-2-carboxylate (108266-34-8)

Guidance literature:

With pyridine; In dichloromethane; for 16h; Ambient temperature;

DOI:10.1021/jo00387a026

Reference yield:

methyl (+)-(1R,2R,3S,5S)-3-hydroxy-7,7-(ethylenedioxy)bicyclo<3.3.0>octane-2-carboxylate (105499-51-2) → (R)-α-methoxy-α-(trifluoromethyl)pnenylacetyl acid ester of methyl (+)-(1R,2R,3S,5S)-3-hydroxy-7-oxobicyclo<3.3.0>octane-2-carboxylate (108168-30-5)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / CH₂Cl₂ / 16 h / Ambient temperature

2: 2N HCl

With pyridine; hydrogenchloride; In dichloromethane;

DOI:10.1021/jo00387a026

upstream raw materials:

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-7,7-(ethylenedioxy)bicyclo<3.3.0>octane-2-carboxylate

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

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

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