(E)-ethyl 3-[(1R,2S,4S)-2-acetoxy-4-methyl-1-cyclohexyl]but-2-enoate

Base Information

• Chemical Name: (E)-ethyl 3-[(1R,2S,4S)-2-acetoxy-4-methyl-1-cyclohexyl]but-2-enoate
• CAS No.: 404367-07-3
• Molecular Formula: C₁₅H₂₄O₄
• Molecular Weight: 268.353
• Mol file: 404367-07-3.mol

Synonyms:(E)-ethyl 3-[(1R,2S,4S)-2-acetoxy-4-methyl-1-cyclohexyl]but-2-enoate

Chemical Property of (E)-ethyl 3-[(1R,2S,4S)-2-acetoxy-4-methyl-1-cyclohexyl]but-2-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-ethyl 3-[(1R,2S,4S)-2-acetoxy-4-methyl-1-cyclohexyl]but-2-enoate

There total 1 articles about (E)-ethyl 3-[(1R,2S,4S)-2-acetoxy-4-methyl-1-cyclohexyl]but-2-enoate 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:

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + (1S,2S,5S)-1-acetoxy-2-acetyl-5-methylcyclohexane → (Z)-ethyl 3-[(1R,2S,4S)-2-acetoxy-4-methyl-1-cyclohexyl]but-2-enoate + (E)-ethyl 3-[(1R,2S,4S)-2-acetoxy-4-methyl-1-cyclohexyl]but-2-enoate (404367-07-3)

Guidance literature:

diethoxyphosphoryl-acetic acid ethyl ester; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 0.333333h;

(1S,2S,5S)-1-acetoxy-2-acetyl-5-methylcyclohexane; In tetrahydrofuran; at 12 ℃; Heating;

DOI:10.1039/b102961b

Reference yield: 90.0%

(E)-ethyl 3-[(1R,2S,4S)-2-acetoxy-4-methyl-1-cyclohexyl]but-2-enoate (404367-07-3) → (3S)-ethyl 3-[(1R,2S,4S)-2-acetoxy-4-methyl-1-cyclohexyl]butanoate (404367-08-4)

Guidance literature:

With sodium tetrahydroborate; Pfaltz's semicorrin; cobalt(II) chloride; In ethanol; N,N-dimethyl-formamide; at 25 ℃; for 144h;

DOI:10.1039/b102961b

Reference yield:

(E)-ethyl 3-[(1R,2S,4S)-2-acetoxy-4-methyl-1-cyclohexyl]but-2-enoate (404367-07-3) → (3S,6R)-6-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-propyl]-2-[1,3]dithian-2-ylidene-3-methyl-1-(2-methyl-allyl)-cyclohexanol (1027322-27-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 90 percent / NaBH₄; CoCl₂*6H₂O; Pfaltz's semicorrin / ethanol; dimethylformamide / 144 h / 25 °C

2.1: 75 percent / DIBAL-H / CH₂Cl₂; hexane / 1 h / -78 - 0 °C

3.1: 95 percent / imidazole / dimethylformamide / 0.25 h

4.1: 5.13 g / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 3.5 h / -65 - 20 °C

5.1: LHMDS; DMPU / tetrahydrofuran; hexane / 0.5 h / -78 °C

5.2: tetrahydrofuran; hexane / 3.5 h / -78 - -20 °C

6.1: LHMDS / tetrahydrofuran; hexane / 0.5 h / -78 °C

6.2: 3.92 g / tetrahydrofuran; hexane / 16 h / -78 - 20 °C

7.1: Mg / tetrahydrofuran

7.2: 4.80 g / tetrahydrofuran / 2 h / 20 °C

With 1H-imidazole; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium tetrahydroborate; oxalyl dichloride; Pfaltz's semicorrin; diisobutylaluminium hydride; magnesium; dimethyl sulfoxide; triethylamine; cobalt(II) chloride; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; 4.1: Swern oxidation;

DOI:10.1039/b102961b

upstream raw materials:

diethoxyphosphoryl-acetic acid ethyl ester

Downstream raw materials:

(3S)-ethyl 3-[(1R,2S,4S)-2-acetoxy-4-methyl-1-cyclohexyl]butanoate

(1S,2R,5S)-2-[(S)-3-hydroxy-1-methylpropyl]-5-methylcyclohexan-1-ol

(1S,2S,5R)-2-[(R)-3-(3-tert-butyldimethylsilyloxy)-1-methylpropyl]-5-methylcyclohexan-1-one

(1S,2S,5R)-2-[(R)-3-(3-tert-butyldimethylsilyloxy)-1-methylpropyl]-5-methylcyclohexan-1-ol