methyl 2-[2-((1S,2S)-2-hydroxy-2,6,6-trimethylcyclohexyl)ethyl]-3-hydroxybutanoate

Base Information

• Chemical Name: methyl 2-[2-((1S,2S)-2-hydroxy-2,6,6-trimethylcyclohexyl)ethyl]-3-hydroxybutanoate
• CAS No.: 680218-13-7
• Molecular Formula: C₁₆H₃₀O₄
• Molecular Weight: 286.412
• Mol file: 680218-13-7.mol

Synonyms:methyl 2-[2-((1S,2S)-2-hydroxy-2,6,6-trimethylcyclohexyl)ethyl]-3-hydroxybutanoate

Chemical Property of methyl 2-[2-((1S,2S)-2-hydroxy-2,6,6-trimethylcyclohexyl)ethyl]-3-hydroxybutanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-[2-((1S,2S)-2-hydroxy-2,6,6-trimethylcyclohexyl)ethyl]-3-hydroxybutanoate

There total 4 articles about methyl 2-[2-((1S,2S)-2-hydroxy-2,6,6-trimethylcyclohexyl)ethyl]-3-hydroxybutanoate 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: 74.0%

acetaldehyde (75-07-0,9002-91-9) + methyl 4-[(1S,2S)-2-hydroxy-2,6,6-trimethylcyclohexyl]butanoate (680218-11-5) → methyl 2-[2-((1S,2S)-2-hydroxy-2,6,6-trimethylcyclohexyl)ethyl]-3-hydroxybutanoate (680218-13-7)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 2.5h;

DOI:10.1081/SCC-120027252

Reference yield:

(-)-(4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalen-1(2H)-one (60134-39-6) → methyl 2-[2-((1S,2S)-2-hydroxy-2,6,6-trimethylcyclohexyl)ethyl]-3-hydroxybutanoate (680218-13-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / m-chloroperoxybenzoic acid; NaHCO₃ / CH₂Cl₂ / 1.5 h / 20 °C

2: sodium hydroxide / ethanol; H₂O / 2.3 h / 20 °C

3: 97 mg / diethyl ether / 0 °C

4: 74 percent / lithium diisopropylamide; hexamethylphosphoramide / tetrahydrofuran / 2.5 h / -78 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; 1: Baeyer-Villiger reaction / 4: aldol condensation;

DOI:10.1081/SCC-120027252

Reference yield:

(1S,7S)-1,8,8-trimethyl-2-oxabicyclo[5.4.0]undecan-3-one (217467-50-0) → methyl 2-[2-((1S,2S)-2-hydroxy-2,6,6-trimethylcyclohexyl)ethyl]-3-hydroxybutanoate (680218-13-7)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydroxide / ethanol; H₂O / 2.3 h / 20 °C

2: 97 mg / diethyl ether / 0 °C

3: 74 percent / lithium diisopropylamide; hexamethylphosphoramide / tetrahydrofuran / 2.5 h / -78 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; ethanol; water; 3: aldol condensation;

DOI:10.1081/SCC-120027252

upstream raw materials:

acetaldehyde

methyl 4-[(1S,2S)-2-hydroxy-2,6,6-trimethylcyclohexyl]butanoate

(-)-(4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalen-1(2H)-one

(1S,7S)-1,8,8-trimethyl-2-oxabicyclo[5.4.0]undecan-3-one

Downstream raw materials:

2-[2-((1S,2S)-2-hydroxy-2,6,6-trimethylcyclohexyl)ethyl]-3-hydroxybutyl 4-methylbenzenesulfonate

2-[2-((1S,2S)-2-hydroxy-2,6,6-trimethylcyclohexyl)ethyl]-3-oxobutyl 4-methylbenzenesulfonate

3-[2-((2S)-2-hydroxy-2,6,6-trimethylcyclohexyl)ethyl]but-3-en-2-one

2-[2-((1S,2S)-2-hydroxy-2,6,6-trimethylcyclohexyl)ethyl]butane-1,3-diol