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

Base Information

• Chemical Name: (+)-2-(4-[(S)-hydroxymethylethyl]-(1S,4R)-cyclohex-2-enyl)propane-1,2,3-triol
• CAS No.: 295356-97-7
• Molecular Formula: C₁₂H₂₂O₄
• Molecular Weight: 230.304

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

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

Chemical Property:

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

There total 2 articles about (+)-2-(4-[(S)-hydroxymethylethyl]-(1S,4R)-cyclohex-2-enyl)propane-1,2,3-triol 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: 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:

(3S,3aS,7aR)-(+)-methyl-2,3,3a,4,5,7a-hexahydrobenzfuran-2-one (145353-87-3) → (+)-2-(4-[(S)-hydroxymethylethyl]-(1S,4R)-cyclohex-2-enyl)propane-1,2,3-triol (295356-97-7)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 72 percent / lithium aluminum hydride / tetrahydrofuran / 5 h / Heating

With palladium diacetate; lithium aluminium tetrahydride; 1,2-bis-(diphenylphosphino)ethane; In tetrahydrofuran; 1: Substitution / 2: Reduction;

DOI:10.1021/jo005516f

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

upstream raw materials:

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

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

Downstream raw materials:

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

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

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

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