(+)-2-[4-[(S)-1-carboxyethyl]-(1S,4R)-cyclohex-2-enyl]-2-(2,2-dimethylpropionyloxy)malonic acid dimethyl ester

Base Information

• Chemical Name: (+)-2-[4-[(S)-1-carboxyethyl]-(1S,4R)-cyclohex-2-enyl]-2-(2,2-dimethylpropionyloxy)malonic acid dimethyl ester
• CAS No.: 295356-96-6
• Molecular Formula: C₁₉H₂₈O₈
• Molecular Weight: 384.427

Synonyms:(+)-2-[4-[(S)-1-carboxyethyl]-(1S,4R)-cyclohex-2-enyl]-2-(2,2-dimethylpropionyloxy)malonic acid dimethyl ester

Chemical Property of (+)-2-[4-[(S)-1-carboxyethyl]-(1S,4R)-cyclohex-2-enyl]-2-(2,2-dimethylpropionyloxy)malonic acid dimethyl ester

Chemical Property:

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Technology Process of (+)-2-[4-[(S)-1-carboxyethyl]-(1S,4R)-cyclohex-2-enyl]-2-(2,2-dimethylpropionyloxy)malonic acid dimethyl ester

There total 1 articles about (+)-2-[4-[(S)-1-carboxyethyl]-(1S,4R)-cyclohex-2-enyl]-2-(2,2-dimethylpropionyloxy)malonic acid dimethyl 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: 88.0%

(3S,3aS,7aR)-(+)-methyl-2,3,3a,4,5,7a-hexahydrobenzfuran-2-one (145353-87-3) + NaC(OCOC4H9)(CO2CH3)2 → (+)-2-[4-[(S)-1-carboxyethyl]-(1S,4R)-cyclohex-2-enyl]-2-(2,2-dimethylpropionyloxy)malonic acid dimethyl ester (295356-96-6)

Guidance literature:

With palladium diacetate; 1,2-bis-(diphenylphosphino)ethane; In tetrahydrofuran; for 3h; Heating;

DOI:10.1021/jo005516f

Reference yield: 72.0%

(+)-2-[4-[(S)-1-carboxyethyl]-(1S,4R)-cyclohex-2-enyl]-2-(2,2-dimethylpropionyloxy)malonic acid dimethyl ester (295356-96-6) → (+)-2-(4-[(S)-hydroxymethylethyl]-(1S,4R)-cyclohex-2-enyl)propane-1,2,3-triol (295356-97-7)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 5h; Heating;

DOI:10.1021/jo005516f

Reference yield:

(+)-2-[4-[(S)-1-carboxyethyl]-(1S,4R)-cyclohex-2-enyl]-2-(2,2-dimethylpropionyloxy)malonic acid dimethyl ester (295356-96-6) → (+)-(4R)-[(S)-methyl-2-oxoethyl]cyclohex-1-enecarboxylic acid methyl ester (295356-99-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 72 percent / lithium aluminum hydride / tetrahydrofuran / 5 h / Heating

2.1: NaIO₄ / H₂O / 2 h / 20 °C

2.2: 54 percent / diethyl ether

3.1: 87 percent / Dess-Martin periodate / CH₂Cl₂ / 0.75 h / 20 °C

With sodium periodate; lithium aluminium tetrahydride; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; water; 1.1: Reduction / 2.1: Oxidation / 2.2: Esterification / 3.1: Oxidation;

DOI:10.1021/jo005516f

upstream raw materials:

(3S,3aS,7aR)-(+)-methyl-2,3,3a,4,5,7a-hexahydrobenzfuran-2-one

Downstream raw materials:

(+)-2-(4-[(S)-hydroxymethylethyl]-(1S,4R)-cyclohex-2-enyl)propane-1,2,3-triol

(+)-(4R)-[(S)-1,5-dimethyl-3-oxohexyl]cyclohex-1-enecarboxylic acid methyl ester

(+)-(4R)-[(S)-methyl-2-oxoethyl]cyclohex-1-enecarboxylic acid methyl ester

(+)-(4R)-4-[(S)-2-hydroxy-1-methylethyl]cyclohex-1-enecarboxylic acid methyl ester

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