2-{(1S,3S,4R)-4-Methyl-3-[2-(2,5,5-trimethyl-[1,3]dioxan-2-yl)-ethyl]-2-[1-trimethylsilanyl-meth-(E)-ylidene]-cyclohexyl}-propionic acid methyl ester

Base Information

• Chemical Name: 2-{(1S,3S,4R)-4-Methyl-3-[2-(2,5,5-trimethyl-[1,3]dioxan-2-yl)-ethyl]-2-[1-trimethylsilanyl-meth-(E)-ylidene]-cyclohexyl}-propionic acid methyl ester
• CAS No.: 116434-65-2
• Molecular Formula: C₂₄H₄₄O₄Si
• Molecular Weight: 424.696

Synonyms:

Chemical Property of 2-{(1S,3S,4R)-4-Methyl-3-[2-(2,5,5-trimethyl-[1,3]dioxan-2-yl)-ethyl]-2-[1-trimethylsilanyl-meth-(E)-ylidene]-cyclohexyl}-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-{(1S,3S,4R)-4-Methyl-3-[2-(2,5,5-trimethyl-[1,3]dioxan-2-yl)-ethyl]-2-[1-trimethylsilanyl-meth-(E)-ylidene]-cyclohexyl}-propionic acid methyl ester

There total 9 articles about 2-{(1S,3S,4R)-4-Methyl-3-[2-(2,5,5-trimethyl-[1,3]dioxan-2-yl)-ethyl]-2-[1-trimethylsilanyl-meth-(E)-ylidene]-cyclohexyl}-propionic acid methyl 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:

2,5,5-trimethyl-2-<2'-(1''(R)-methyl-3''-oxocyclohex-2''-yl)ethyl>-1,3-dioxane (116399-89-4) → 2-{(1S,3S,4R)-4-Methyl-3-[2-(2,5,5-trimethyl-[1,3]dioxan-2-yl)-ethyl]-2-[1-trimethylsilanyl-meth-(E)-ylidene]-cyclohexyl}-propionic acid methyl ester (116434-65-2,116502-41-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 94 percent / pyridine / tetrahydrofuran / Heating

2: 1.) n-BuLi, TMEDA, 2.) DMF

3: 1.) Et₂O, pentane, -78 deg C, 2.) DMAP, 20 deg C

4: 56 percent / LICA / tetrahydrofuran / -78 deg C to 20 deg C

5: 94 percent / K₂CO₃ / acetone

6: 1.) LICA / 1.) THF, 0 deg C, 2.) 0 deg C

With pyridine; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; lithium cyclohexylisopropylamide; potassium carbonate; N,N-dimethyl-formamide; In tetrahydrofuran; acetone;

DOI:10.1016/S0040-4039(00)96582-1

Reference yield:

2-(2,5,5-trimethyl-1,3-dioxan-2-yl)ethyl bromide (87842-52-2) → 2-{(1S,3S,4R)-4-Methyl-3-[2-(2,5,5-trimethyl-[1,3]dioxan-2-yl)-ethyl]-2-[1-trimethylsilanyl-meth-(E)-ylidene]-cyclohexyl}-propionic acid methyl ester (116434-65-2,116502-41-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) LDA, HMPA / 1.) THF, -78 deg C

2: Al(Hg) / tetrahydrofuran; H₂O

3: 94 percent / pyridine / tetrahydrofuran / Heating

4: 1.) n-BuLi, TMEDA, 2.) DMF

5: 1.) Et₂O, pentane, -78 deg C, 2.) DMAP, 20 deg C

6: 56 percent / LICA / tetrahydrofuran / -78 deg C to 20 deg C

7: 94 percent / K₂CO₃ / acetone

8: 1.) LICA / 1.) THF, 0 deg C, 2.) 0 deg C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; aluminum amalgam; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; lithium cyclohexylisopropylamide; potassium carbonate; N,N-dimethyl-formamide; lithium diisopropyl amide; In tetrahydrofuran; water; acetone;

DOI:10.1016/S0040-4039(00)96582-1

Reference yield:

(5R)-5-methyl-2-(phenylsulfinyl)cyclohexan-1-one (88154-77-2) → 2-{(1S,3S,4R)-4-Methyl-3-[2-(2,5,5-trimethyl-[1,3]dioxan-2-yl)-ethyl]-2-[1-trimethylsilanyl-meth-(E)-ylidene]-cyclohexyl}-propionic acid methyl ester (116434-65-2,116502-41-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) LDA, HMPA / 1.) THF, -78 deg C

2: Al(Hg) / tetrahydrofuran; H₂O

3: 94 percent / pyridine / tetrahydrofuran / Heating

4: 1.) n-BuLi, TMEDA, 2.) DMF

5: 1.) Et₂O, pentane, -78 deg C, 2.) DMAP, 20 deg C

6: 56 percent / LICA / tetrahydrofuran / -78 deg C to 20 deg C

7: 94 percent / K₂CO₃ / acetone

8: 1.) LICA / 1.) THF, 0 deg C, 2.) 0 deg C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; aluminum amalgam; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; lithium cyclohexylisopropylamide; potassium carbonate; N,N-dimethyl-formamide; lithium diisopropyl amide; In tetrahydrofuran; water; acetone;

DOI:10.1016/S0040-4039(00)96582-1

upstream raw materials:

{(1S,3S,4R)-4-Methyl-3-[2-(2,5,5-trimethyl-[1,3]dioxan-2-yl)-ethyl]-2-[1-trimethylsilanyl-meth-(Z)-ylidene]-cyclohexyl}-acetic acid methyl ester

methyl iodide

2,5,5-trimethyl-2-<2'-(1''(R)-methyl-3''-oxocyclohex-2''-yl)ethyl>-1,3-dioxane

2-(2,5,5-trimethyl-1,3-dioxan-2-yl)ethyl bromide

Downstream raw materials:

(2R,1'S,3'S,4'S)-2-<4'-methyl-3'-(3''-oxobutyl)-2'(E)-<(trimethylsilyl)methylene>cyclohexyl>propionic acid

(S)-2-{(1S,3S,4R)-4-Methyl-3-(3-oxo-butyl)-2-[1-trimethylsilanyl-meth-(E)-ylidene]-cyclohexyl}-propionic acid

(+)-9-isoartemisinin

C₁₂H₁₃O₂(CH₃)3(O)(OO)

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