(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (2R,3E)-2-hydroxy-3-octadecenoate

Base Information

• Chemical Name: (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (2R,3E)-2-hydroxy-3-octadecenoate
• CAS No.: 150178-55-5
• Molecular Formula: C₃₄H₅₆O₃
• Molecular Weight: 512.817
• Mol file: 150178-55-5.mol

Synonyms:(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (2R,3E)-2-hydroxy-3-octadecenoate

Chemical Property of (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (2R,3E)-2-hydroxy-3-octadecenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (2R,3E)-2-hydroxy-3-octadecenoate

There total 3 articles about (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (2R,3E)-2-hydroxy-3-octadecenoate 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:

(E)-2-Oxo-octadec-3-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester (150178-57-7) → (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (2R,3E)-2-hydroxy-3-octadecenoate (150178-55-5)

Guidance literature:

With sodium hydroxide; dihydrogen peroxide; L-Selectride; Yield given. Multistep reaction; 1.) Et₂O, -78 deg C, 1 h, 2.) MeOH, -78 deg C to r.t., 1 h;

DOI:10.1021/jo00068a056

Reference yield:

pentadecanol (629-76-5) → (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (2R,3E)-2-hydroxy-3-octadecenoate (150178-55-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) PCC, 2.) H⁽¹⁺⁾

2: 1.) BF₃*OEt₂, 2.) SiO₂ / 1.) CH₂Cl₂, -78 to 0 deg C, 2.) C₆H₆, reflux

4: 1.) L-selectride, 2.) 10percent aq. NaOH, 30percent aq. H₂O₂ / 1.) Et₂O, -78 deg C, 1 h, 2.) MeOH, -78 deg C to r.t., 1 h

With sodium hydroxide; boron trifluoride diethyl etherate; dihydrogen peroxide; silica gel; hydrogen cation; L-Selectride; pyridinium chlorochromate;

DOI:10.1021/jo00068a056

Reference yield:

ethyl (E)-2-oxo-3-octadecenoate (1027208-67-8) → (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (2R,3E)-2-hydroxy-3-octadecenoate (150178-55-5)

Guidance literature:

Multi-step reaction with 2 steps

2: 1.) L-selectride, 2.) 10percent aq. NaOH, 30percent aq. H₂O₂ / 1.) Et₂O, -78 deg C, 1 h, 2.) MeOH, -78 deg C to r.t., 1 h

With sodium hydroxide; dihydrogen peroxide; L-Selectride;

DOI:10.1021/jo00068a056

upstream raw materials:

(E)-2-Oxo-octadec-3-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

pentadecanol

ethyl (E)-2-oxo-3-octadecenoate

Downstream raw materials:

(-)-8-phenylmenthol

methyl (2'R,3'E)-2'-hydroxyoctadec-3'-enoate

Refernces