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

Base Information

• Chemical Name: (E)-(2S,3S)-5-((1R,3R,4R)-3-Methoxy-4-triisopropylsilanyloxy-cyclohexyl)-2,4-dimethyl-3-triethylsilanyloxy-pent-4-enal
• CAS No.: 116386-65-3
• Molecular Formula: C₂₉H₅₈O₄Si₂
• Molecular Weight: 526.948
• Mol file: 116386-65-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 21 articles about (E)-(2S,3S)-5-((1R,3R,4R)-3-Methoxy-4-triisopropylsilanyloxy-cyclohexyl)-2,4-dimethyl-3-triethylsilanyloxy-pent-4-enal 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: 86.0%

(E)-(2S,3S)-5-((1R,3R,4R)-3-Methoxy-4-triisopropylsilanyloxy-cyclohexyl)-2,4-dimethyl-3-triethylsilanyloxy-pent-4-enoic acid methoxy-methyl-amide (126788-81-6) → (E)-(2S,3S)-5-((1R,3R,4R)-3-Methoxy-4-triisopropylsilanyloxy-cyclohexyl)-2,4-dimethyl-3-triethylsilanyloxy-pent-4-enal (116386-65-3)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; at -78 ℃;

DOI:10.1021/ja00164a023

Reference yield:

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → (E)-(2S,3S)-5-((1R,3R,4R)-3-Methoxy-4-triisopropylsilanyloxy-cyclohexyl)-2,4-dimethyl-3-triethylsilanyloxy-pent-4-enal (116386-65-3)

Guidance literature:

Multi-step reaction with 7 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

6: n-Bu₂BOTf, diisopropylethylamine / CH₂Cl₂ / 2 h / -78 - 0 °C

With 2,6-dimethylpyridine; 2,6-di-tert-butyl-4-methylpyridine; di-n-butylboryl trifluoromethanesulfonate; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; toluene;

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

Reference yield:

1,2,5,6-tetrahydrobenzoic acid (4771-80-6) → (E)-(2S,3S)-5-((1R,3R,4R)-3-Methoxy-4-triisopropylsilanyloxy-cyclohexyl)-2,4-dimethyl-3-triethylsilanyloxy-pent-4-enal (116386-65-3)

Guidance literature:

Multi-step reaction with 11 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

8: 1.) Et₃N, n-Bu₂BOTf / 1.) -70 deg C, 2.) -50 deg C

9: 1.) Al(CH₃)3 / 1.) CH₂Cl₂, 0 deg C, 2.) -10 deg C to 20 deg C

10: 2,6-lutidine / CH₂Cl₂ / 0 °C

11: 86 percent / DIBAL / tetrahydrofuran / -78 °C

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

DOI:10.1021/ja00164a023

upstream raw materials:

triethylsilyl trifluoromethyl sulfonate

(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

(E)-(2S,3S)-5-((1R,3R,4R)-3-Methoxy-4-triisopropylsilanyloxy-cyclohexyl)-2,4-dimethyl-3-triethylsilanyloxy-pent-4-enoic acid methoxy-methyl-amide

triisopropylsilyl trifluoromethanesulfonate

Downstream raw materials:

(S)-4-Benzyl-3-[(E)-(2S,3R,4R,5S)-2-chloro-3-hydroxy-7-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-4,6-dimethyl-5-triethylsilanyloxy-hept-6-enoyl]-oxazolidin-2-one

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

(S)-4-Benzyl-3-[(E)-(3S,4R,5S)-3-hydroxy-7-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-4,6-dimethyl-5-triethylsilanyloxy-hept-6-enoyl]-oxazolidin-2-one

(E)-(3S,4R,5S)-7-((1R,3R,4R)-3-Methoxy-4-triisopropylsilanyloxy-cyclohexyl)-4,6-dimethyl-5-triethylsilanyloxy-3-triisopropylsilanyloxy-hept-6-enoic acid methoxy-methyl-amide