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

Base Information

• Chemical Name: (E)-(2S,3S)-5-((1R,3R,4R)-3-Methoxy-4-triisopropylsilanyloxy-cyclohexyl)-2,4-dimethyl-3-triethylsilanyloxy-pent-4-enoic acid methoxy-methyl-amide
• CAS No.: 126788-81-6
• Molecular Formula: C₃₁H₆₃NO₅Si₂
• Molecular Weight: 586.016
• Mol file: 126788-81-6.mol

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

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

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-enoic acid methoxy-methyl-amide

There total 10 articles about (E)-(2S,3S)-5-((1R,3R,4R)-3-Methoxy-4-triisopropylsilanyloxy-cyclohexyl)-2,4-dimethyl-3-triethylsilanyloxy-pent-4-enoic acid methoxy-methyl-amide 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:

triethylsilyl trifluoromethyl sulfonate (79271-56-0) + (E)-(2S,3S)-3-Hydroxy-5-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-2,4-dimethyl-pent-4-enoic acid methoxy-methyl-amide (126788-80-5) → (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)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; Yield given;

DOI:10.1021/ja00164a023

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-enoic acid methoxy-methyl-amide (126788-81-6)

Guidance literature:

Multi-step reaction with 10 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

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

Reference yield:

3,4-Dihydroxycyclohexanecarboxylic acid-γ-lactone (88255-83-8,116498-92-1,126873-60-7) → (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)

Guidance literature:

Multi-step reaction with 8 steps

1: 2,6-lutidine / CH₂Cl₂ / 0 °C

2: Al(CH₃)3 / toluene / 20 °C

3: 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 20 °C

4: DIBAL / tetrahydrofuran / -78 °C

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

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

8: 2,6-lutidine / CH₂Cl₂ / 0 °C

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

DOI:10.1021/ja00164a023

upstream raw materials:

triethylsilyl trifluoromethyl sulfonate

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

1,2,5,6-tetrahydrobenzoic acid

3,4-Dihydroxycyclohexanecarboxylic acid-γ-lactone

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

(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

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