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

Base Information

• Chemical Name: (+)-(4R)-4-[(S)-2-hydroxy-1-methylethyl]cyclohex-1-enecarboxylic acid methyl ester
• CAS No.: 295356-98-8
• Molecular Formula: C₁₁H₁₈O₃
• Molecular Weight: 198.262

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

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

Chemical Property:

Purity/Quality:

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

There total 3 articles about (+)-(4R)-4-[(S)-2-hydroxy-1-methylethyl]cyclohex-1-enecarboxylic acid methyl 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: 54.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + (+)-2-(4-[(S)-hydroxymethylethyl]-(1S,4R)-cyclohex-2-enyl)propane-1,2,3-triol (295356-97-7) → (+)-(4R)-4-[(S)-2-hydroxy-1-methylethyl]cyclohex-1-enecarboxylic acid methyl ester (295356-98-8)

Guidance literature:

(+)-2-(4-[(S)-hydroxymethylethyl]-(1S,4R)-cyclohex-2-enyl)propane-1,2,3-triol; With sodium periodate; In water; at 20 ℃; for 2h;

diazomethane; In diethyl ether; Further stages.;

DOI:10.1021/jo005516f

Reference yield:

(3S,3aS,7aR)-(+)-methyl-2,3,3a,4,5,7a-hexahydrobenzfuran-2-one (145353-87-3) → (+)-(4R)-4-[(S)-2-hydroxy-1-methylethyl]cyclohex-1-enecarboxylic acid methyl ester (295356-98-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 88 percent / Pd(OAc)2; 1,2-bis(diphenylphosphino)ethane / tetrahydrofuran / 3 h / Heating

2.1: 72 percent / lithium aluminum hydride / tetrahydrofuran / 5 h / Heating

3.1: NaIO₄ / H₂O / 2 h / 20 °C

3.2: 54 percent / diethyl ether

With palladium diacetate; sodium periodate; lithium aluminium tetrahydride; 1,2-bis-(diphenylphosphino)ethane; In tetrahydrofuran; water; 1.1: Substitution / 2.1: Reduction / 3.1: Oxidation / 3.2: Esterification;

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)-4-[(S)-2-hydroxy-1-methylethyl]cyclohex-1-enecarboxylic acid methyl ester (295356-98-8)

Guidance literature:

Multi-step reaction with 2 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

With sodium periodate; lithium aluminium tetrahydride; In tetrahydrofuran; water; 1.1: Reduction / 2.1: Oxidation / 2.2: Esterification;

DOI:10.1021/jo005516f

upstream raw materials:

diazomethane

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

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

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

Downstream raw materials:

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

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

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