(E)-2-Methyl-3-<(1R,3R,4R)-3-methoxy-4-<(triisopropylsilyl)oxy>cyclohexyl>-2-propenal

Base Information

• Chemical Name: (E)-2-Methyl-3-<(1R,3R,4R)-3-methoxy-4-<(triisopropylsilyl)oxy>cyclohexyl>-2-propenal
• CAS No.: 116386-63-1
• Molecular Formula: C₂₀H₃₈O₃Si
• Molecular Weight: 354.605
• Mol file: 116386-63-1.mol

Synonyms:(E)-2-Methyl-3-<(1R,3R,4R)-3-methoxy-4-<(triisopropylsilyl)oxy>cyclohexyl>-2-propenal

Chemical Property of (E)-2-Methyl-3-<(1R,3R,4R)-3-methoxy-4-<(triisopropylsilyl)oxy>cyclohexyl>-2-propenal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-2-Methyl-3-<(1R,3R,4R)-3-methoxy-4-<(triisopropylsilyl)oxy>cyclohexyl>-2-propenal

There total 23 articles about (E)-2-Methyl-3-<(1R,3R,4R)-3-methoxy-4-<(triisopropylsilyl)oxy>cyclohexyl>-2-propenal 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: 78.0%

(1R,3R,4R)-3-methoxy-4-<(triisopropylsilyl)oxy>cyclohexanecarboxaldehyde (116386-61-9) + 2-lithio-2-triethylsilylpropanal t-butylimine → (E)-2-Methyl-3-<(1R,3R,4R)-3-methoxy-4-<(triisopropylsilyl)oxy>cyclohexyl>-2-propenal (116386-63-1)

Guidance literature:

In tetrahydrofuran; at -78 - -10 ℃;

DOI:10.1016/S0040-4039(00)80074-X

Reference yield:

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → (E)-2-Methyl-3-<(1R,3R,4R)-3-methoxy-4-<(triisopropylsilyl)oxy>cyclohexyl>-2-propenal (116386-63-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 2,6-lutidine / CH₂Cl₂ / 0 °C

2: toluene

3: 2,6-di-t-butyl-4-methyl pyridine / CH₂Cl₂ / 24 h / 22 - 24 °C

4: (iBu)2AlH / tetrahydrofuran / 1 h / -75 °C

5: 78 percent / tetrahydrofuran / -78 - -10 °C

With 2,6-dimethylpyridine; 2,6-di-tert-butyl-4-methylpyridine; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1016/S0040-4039(00)80074-X

Reference yield:

1,2,5,6-tetrahydrobenzoic acid (4771-80-6) → (E)-3-((1R,3R,4R)-3-Methoxy-4-triisopropylsilanyloxy-cyclohexyl)-2-methyl-propenal (116386-63-1,119816-12-5,119816-13-6,126873-62-9)

Guidance literature:

Multi-step reaction with 7 steps

1: m-CPBA / CH₂Cl₂ / 0 °C

2: chlorobenzene / 130 °C

3: 2,6-lutidine / CH₂Cl₂ / 0 °C

4: Al(CH₃)3 / toluene / 20 °C

5: 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 20 °C

6: DIBAL / tetrahydrofuran / -78 °C

With 2,6-dimethylpyridine; 2,6-di-tert-butyl-4-methylpyridine; trimethylaluminum; diisobutylaluminium hydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; chlorobenzene; toluene;

DOI:10.1021/ja00164a023

upstream raw materials:

(1R,3R,4R)-3-Methoxy-4-triisopropylsilanyloxy-cyclohexanecarbaldehyde

1,2,5,6-tetrahydrobenzoic acid

3,4-Dihydroxycyclohexanecarboxylic acid-γ-lactone

(1S,3R)-7-Oxa-bicyclo[4.1.0]heptane-3-carboxylic acid

Downstream raw materials:

(E)-(3S,4R,5S)-3-Hydroxy-7-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-4,6-dimethyl-5-triethylsilanyloxy-hept-6-enoic acid (S)-2-hydroxy-1,2,2-triphenyl-ethyl ester

(E)-(3S,4R,5S)-7-((1R,3R,4R)-3-Methoxy-4-triisopropylsilanyloxy-cyclohexyl)-4,6-dimethyl-5-triethylsilanyloxy-3-triisopropylsilanyloxy-hept-6-enal

(E)-(2S,3S)-5-((1R,3R,4R)-3-Methoxy-4-triisopropylsilanyloxy-cyclohexyl)-2,4-dimethyl-3-triethylsilanyloxy-pent-4-enal

(S)-3-[(E)-(2S,3S)-3-Hydroxy-5-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-2,4-dimethyl-pent-4-enoyl]-4-isopropyl-oxazolidin-2-one