2-Propenoic acid, 3-[(2S)-tetrahydro-6-hydroxy-2H-pyran-2-yl]-, (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester, (2Z)-

Base Information

• Chemical Name: 2-Propenoic acid, 3-[(2S)-tetrahydro-6-hydroxy-2H-pyran-2-yl]-, (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester, (2Z)-
• CAS No.: 837428-46-3
• Molecular Formula: C24H34O4
• Molecular Weight: 386.532
• Mol file: 837428-46-3.mol

Synonyms:

Chemical Property of 2-Propenoic acid, 3-[(2S)-tetrahydro-6-hydroxy-2H-pyran-2-yl]-, (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester, (2Z)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Propenoic acid, 3-[(2S)-tetrahydro-6-hydroxy-2H-pyran-2-yl]-, (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester, (2Z)-

There total 1 articles about 2-Propenoic acid, 3-[(2S)-tetrahydro-6-hydroxy-2H-pyran-2-yl]-, (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester, (2Z)- 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: 52.0%

(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (2Z)-3-[3,4-dihydro-2H-pyran-2-yl]acrylate → (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (2S)-3-[(2S)-6-hydroxytetrahydro-2H-pyran-2-yl]acrylate (837428-46-3)

Guidance literature:

With toluene-4-sulfonic acid; In tetrahydrofuran; at 32 ℃; for 20h;

DOI:10.1021/jo052233k

Reference yield: 74.0%

(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (2S)-3-[(2S)-6-hydroxytetrahydro-2H-pyran-2-yl]acrylate (837428-46-3) + benzyl diethylphosphonoacetate (7396-44-3) → 10-benzyl 1-[(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl] (2Z,4S,8E)-4-hydroxydeca-2,8-dienedioate (881663-82-7)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; toluene; at 0 ℃; for 14h;

DOI:10.1021/jo052233k

Reference yield:

(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (2S)-3-[(2S)-6-hydroxytetrahydro-2H-pyran-2-yl]acrylate (837428-46-3) → 10-benzyl 1-[(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl] (2Z,4S,8E)-4-[(diphenylphosphoryl)oxy]deca-2,8-dienedioate (881663-83-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / LiHMDS / tetrahydrofuran; toluene / 14 h / 0 °C

2: 86 percent / imidazole / 1,2-dichloro-ethane; tetrahydrofuran / 16 h / 60 °C

With 1H-imidazole; lithium hexamethyldisilazane; In tetrahydrofuran; 1,2-dichloro-ethane; toluene; 1: Horner-Wadsworth-Emmons reaction;

DOI:10.1021/jo052233k

Downstream raw materials:

10-benzyl 1-[(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl] (2Z,4S,8E)-4-hydroxydeca-2,8-dienedioate

10-benzyl 1-[(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl] (2Z,4S,8E)-4-[(diphenylphosphoryl)oxy]deca-2,8-dienedioate