methyl (1R,2S,6S)-6-isopropyl-3-methyl-5-oxo-2-(4-oxobutyl)cyclohex-3-enecarboxylate

Base Information

• Chemical Name: methyl (1R,2S,6S)-6-isopropyl-3-methyl-5-oxo-2-(4-oxobutyl)cyclohex-3-enecarboxylate
• CAS No.: 1375478-81-1
• Molecular Formula: C₁₆H₂₄O₄
• Molecular Weight: 280.364

Synonyms:methyl (1R,2S,6S)-6-isopropyl-3-methyl-5-oxo-2-(4-oxobutyl)cyclohex-3-enecarboxylate

Chemical Property of methyl (1R,2S,6S)-6-isopropyl-3-methyl-5-oxo-2-(4-oxobutyl)cyclohex-3-enecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (1R,2S,6S)-6-isopropyl-3-methyl-5-oxo-2-(4-oxobutyl)cyclohex-3-enecarboxylate

There total 15 articles about methyl (1R,2S,6S)-6-isopropyl-3-methyl-5-oxo-2-(4-oxobutyl)cyclohex-3-enecarboxylate 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: 76.0%

methyl (1R,2S,5R,6S)-5-hydroxy-2-(4-hydroxybutyl)-6-isopropyl-3-methylcyclohex-3-enecarboxylate (1375478-80-0) → methyl (1R,2S,6S)-6-isopropyl-3-methyl-5-oxo-2-(4-oxobutyl)cyclohex-3-enecarboxylate (1375478-81-1)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; at 0 - 20 ℃; for 2.5h; Inert atmosphere; Celite;

DOI:10.1002/anie.201108564

Reference yield:

C15H22O4 (1375478-66-2) → methyl (1R,2S,6S)-6-isopropyl-3-methyl-5-oxo-2-(4-oxobutyl)cyclohex-3-enecarboxylate (1375478-81-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 1H-imidazole; dmap / dichloromethane / 0 - 20 °C / Inert atmosphere

2.1: pyridine; hydrogen fluoride / tetrahydrofuran / 7 h / 0 - 20 °C / Inert atmosphere

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

3.2: -78 - 20 °C / Inert atmosphere

4.1: tert.-butyl lithium / diethyl ether; pentane / 0.08 h / -78 °C / Inert atmosphere

4.2: 0.67 h / 0 °C / Inert atmosphere

4.3: 3.5 h / 0 - 20 °C / Inert atmosphere

5.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 20 °C / Inert atmosphere

6.1: n-butyllithium; chloro-trimethyl-silane; triethylamine; diisopropylamine / tetrahydrofuran; hexanes / -78 - 20 °C / Inert atmosphere

6.2: 120 °C / Inert atmosphere

7.1: methanol; diethyl ether; benzene / 1.5 h / 6 - 20 °C / Inert atmosphere

8.1: pyridine; hydrogen fluoride / tetrahydrofuran / 24 h / 0 - 20 °C / Inert atmosphere

9.1: pyridinium chlorochromate / dichloromethane / 2.5 h / 0 - 20 °C / Inert atmosphere; Celite

With pyridine; 1H-imidazole; dmap; n-butyllithium; chloro-trimethyl-silane; oxalyl dichloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; hydrogen fluoride; tert.-butyl lithium; dimethyl sulfoxide; triethylamine; diisopropylamine; pyridinium chlorochromate; In tetrahydrofuran; methanol; hexanes; diethyl ether; dichloromethane; pentane; benzene; 6.1: Ireland-Claisen rearrangement / 6.2: Ireland-Claisen rearrangement;

DOI:10.1002/anie.201108564

Reference yield:

(3R,4R,5S,E)-4-((tert-butyldimethylsilyl)oxy)-11-((tert-butyldiphenylsilyl)oxy)-3-isopropyl-6-methylundec-6-ene-1,5-diol (1375478-74-2) → methyl (1R,2S,6S)-6-isopropyl-3-methyl-5-oxo-2-(4-oxobutyl)cyclohex-3-enecarboxylate (1375478-81-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 20 °C / Inert atmosphere

2.1: n-butyllithium; chloro-trimethyl-silane; triethylamine; diisopropylamine / tetrahydrofuran; hexanes / -78 - 20 °C / Inert atmosphere

2.2: 120 °C / Inert atmosphere

3.1: methanol; diethyl ether; benzene / 1.5 h / 6 - 20 °C / Inert atmosphere

4.1: pyridine; hydrogen fluoride / tetrahydrofuran / 24 h / 0 - 20 °C / Inert atmosphere

5.1: pyridinium chlorochromate / dichloromethane / 2.5 h / 0 - 20 °C / Inert atmosphere; Celite

With pyridine; n-butyllithium; chloro-trimethyl-silane; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; hydrogen fluoride; triethylamine; diisopropylamine; pyridinium chlorochromate; In tetrahydrofuran; methanol; hexanes; diethyl ether; dichloromethane; benzene; 2.1: Ireland-Claisen rearrangement / 2.2: Ireland-Claisen rearrangement;

DOI:10.1002/anie.201108564

upstream raw materials:

C₁₈H₂₆O₄

C₁₅H₂₂O₄

(3R,4R)-4-((tert-butyldimethylsilyl)oxy)-5-hydroxy-3-isopropylpentyl benzoate

ethyl (R)-3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-methylpentanoate

Downstream raw materials:

dendrobine

C₃₄H₄₉NO₄Si

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