Acetic acid, dihydroxy-, (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

Base Information

• Chemical Name: Acetic acid, dihydroxy-, (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester
• CAS No.: 108794-12-3
• Molecular Formula: C18H26O4
• Molecular Weight: 306.402
• DSSTox Substance ID: DTXSID301124759
• Nikkaji Number: J329.310F
• Mol file: 108794-12-3.mol

Synonyms:DTXSID301124759;Acetic acid, dihydroxy-, (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester;108794-12-3

Chemical Property of Acetic acid, dihydroxy-, (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

Chemical Property:

• XLogP3: 3.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 306.18310931
• Heavy Atom Count: 22
• Complexity: 371

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1CCC(C(C1)OC(=O)C(O)O)C(C)(C)C2=CC=CC=C2
• Isomeric SMILES: C[C@@H]1CC[C@H]([C@@H](C1)OC(=O)C(O)O)C(C)(C)C2=CC=CC=C2

Technology Process of Acetic acid, dihydroxy-, (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

There total 6 articles about Acetic acid, dihydroxy-, (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl 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: 95.0%

bromoacetic acid (-)-8-phenylmenthol ester (80595-59-1) → <1R-(1α,2β,5α)>-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl dihydroxyacetate (108794-12-3)

Guidance literature:

With sodium acetate; In dimethyl sulfoxide;

DOI:10.1016/S0040-4039(00)86707-6

Reference yield:

(-)-8-phenylmenthol (65253-04-5) → <1R-(1α,2β,5α)>-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl dihydroxyacetate (108794-12-3)

Guidance literature:

Multi-step reaction with 2 steps

1: CHCl₃ / 2 h / Ambient temperature

2: Bu₃SnH / Pd(Ph₃P)4 / 1.) PhH, r.t., 2 h, 2.) PhH, CH₂Cl₂, reflux, 1 h

With tri-n-butyl-tin hydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In chloroform;

DOI:10.1055/s-1998-2198

Reference yield:

(-)-8-phenylmenthyl acrylate (72526-00-2) → (1R,3R,4S)-8-phenylmenthyl glyoxylate (84312-20-9) + <1R-(1α,2β,5α)>-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl dihydroxyacetate (108794-12-3)

Guidance literature:

With sodium periodate; osmium(VIII) oxide; In 1,4-dioxane; water; tert-butyl alcohol; for 2h;

DOI:10.1016/S0040-4020(98)01140-5

upstream raw materials:

bromoacetic acid (-)-8-phenylmenthol ester

Chloro-oxo-acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

(-)-8-phenylmenthyl acrylate

(-)-8-phenylmenthol

Downstream raw materials:

O-[(2S)-hydroxy-3-nitropropanoyl]-(1'R,2'S,5'R)-8'-phenylmenthol

8-Phenylmenthyl (2S,3R)-5-Methyl-3-nitro-2-((triethylsilyl)oxy)hexanoate

8-Phenylmenthyl (2R,3S)-2-Hydroxy-5-methyl-3-nitro-hexanoate

8-Phenylmenthyl (2S,3S)-2-Hydroxy-5-methyl-3-nitro-hexanoate