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

Base Information

• Chemical Name: (2R,1'S,3'S,4'S)-2-<4'-methyl-3'-(3''-oxobutyl)-2'(E)-<(trimethylsilyl)methylene>cyclohexyl>propionic acid
• CAS No.: 116399-93-0
• Molecular Formula: C₁₈H₃₂O₃Si
• Molecular Weight: 324.536
• Mol file: 116399-93-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about (2R,1'S,3'S,4'S)-2-<4'-methyl-3'-(3''-oxobutyl)-2'(E)-<(trimethylsilyl)methylene>cyclohexyl>propionic acid 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: 81.0%

2,5,5-trimethyl-2-<2'-<4''-(1(S)-carboxyethyl)-1''(R)-methyl-3''-<(trimethylsilyl)methylene>cyclohex-2''-yl>ethyl>-1,3-dioxane (116400-02-3) → (2R,1'S,3'S,4'S)-2-<4'-methyl-3'-(3''-oxobutyl)-2'(E)-<(trimethylsilyl)methylene>cyclohexyl>propionic acid (116399-93-0)

Guidance literature:

With oxalic acid; silica gel; In dichloromethane; for 20h;

DOI:10.1021/ja00029a028

Reference yield:

2,5,5-trimethyl-2-<2'-((1''S)-2''-formyl-6''(R)-methylcyclohex-2''-enyl)ethyl>-1,3-dioxane (116399-90-7) → (2R,1'S,3'S,4'S)-2-<4'-methyl-3'-(3''-oxobutyl)-2'(E)-<(trimethylsilyl)methylene>cyclohexyl>propionic acid (116399-93-0)

Guidance literature:

Multi-step reaction with 5 steps

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

2: 56 percent / LICA / tetrahydrofuran / -78 deg C to 20 deg C

3: 94 percent / K₂CO₃ / acetone

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

5: 1.) KOH, 2.) aq. oxalic acid, silicagel / 1.) MeOH, 2.) CH₂Cl₂, 20 deg C

With potassium hydroxide; oxalic acid; silica gel; lithium cyclohexylisopropylamide; potassium carbonate; In tetrahydrofuran; acetone;

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

Reference yield:

2,5,5-trimethyl-2-<2'-<1''R-methyl-3''-<(trimethylsilyl)hydroxymethyl>cyclohex-3''-en-2''-yl>ethyl>-1,3-dioxane acetyl ester (116399-91-8) → (2R,1'S,3'S,4'S)-2-<4'-methyl-3'-(3''-oxobutyl)-2'(E)-<(trimethylsilyl)methylene>cyclohexyl>propionic acid (116399-93-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 56 percent / LICA / tetrahydrofuran / -78 deg C to 20 deg C

2: 94 percent / K₂CO₃ / acetone

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

4: 1.) KOH, 2.) aq. oxalic acid, silicagel / 1.) MeOH, 2.) CH₂Cl₂, 20 deg C

With potassium hydroxide; oxalic acid; silica gel; lithium cyclohexylisopropylamide; potassium carbonate; In tetrahydrofuran; acetone;

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

upstream raw materials:

2,5,5-trimethyl-2-<2'-<4''-(1(S)-carboxyethyl)-1''(R)-methyl-3''-<(trimethylsilyl)methylene>cyclohex-2''-yl>ethyl>-1,3-dioxane

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

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

(5R)-5-methyl-2-(phenylsulfinyl)cyclohexan-1-one

Downstream raw materials:

C₁₂H₁₃O₂(CH₃)3(O)(OO)

2-deoxyartemisinin