5-((Z)-Hex-3-ene-1,5-diynyl)-3,6,6-trimethoxy-5-triethylsilanyloxy-cyclohexa-1,3-dienecarbaldehyde

Base Information

• Chemical Name: 5-((Z)-Hex-3-ene-1,5-diynyl)-3,6,6-trimethoxy-5-triethylsilanyloxy-cyclohexa-1,3-dienecarbaldehyde
• CAS No.: 204848-99-7
• Molecular Formula: C₂₂H₃₀O₅Si
• Molecular Weight: 402.563
• Mol file: 204848-99-7.mol

Synonyms:5-((Z)-Hex-3-ene-1,5-diynyl)-3,6,6-trimethoxy-5-triethylsilanyloxy-cyclohexa-1,3-dienecarbaldehyde

Chemical Property of 5-((Z)-Hex-3-ene-1,5-diynyl)-3,6,6-trimethoxy-5-triethylsilanyloxy-cyclohexa-1,3-dienecarbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-((Z)-Hex-3-ene-1,5-diynyl)-3,6,6-trimethoxy-5-triethylsilanyloxy-cyclohexa-1,3-dienecarbaldehyde

There total 9 articles about 5-((Z)-Hex-3-ene-1,5-diynyl)-3,6,6-trimethoxy-5-triethylsilanyloxy-cyclohexa-1,3-dienecarbaldehyde 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:

[5-((Z)-Hex-3-ene-1,5-diynyl)-3,6,6-trimethoxy-5-triethylsilanyloxy-cyclohexa-1,3-dienyl]-methanol (204848-98-6) → 5-((Z)-Hex-3-ene-1,5-diynyl)-3,6,6-trimethoxy-5-triethylsilanyloxy-cyclohexa-1,3-dienecarbaldehyde (204848-99-7)

Guidance literature:

With Dess-Martin periodane; Yield given;

DOI:10.1021/ja9801543

Reference yield:

5-((Z)-Hex-3-ene-1,5-diynyl)-3,6,6-trimethoxy-5-triethylsilanyloxy-cyclohexa-1,3-dienecarboxylic acid ethyl ester (204848-97-5) → 5-((Z)-Hex-3-ene-1,5-diynyl)-3,6,6-trimethoxy-5-triethylsilanyloxy-cyclohexa-1,3-dienecarbaldehyde (204848-99-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 18.6 g / DIBAL-H / toluene / 1.5 h / -78 °C

2: NaHCO₃, 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3-(1H)-one / CH₂Cl₂ / 0.5 h / 0 °C

With diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; toluene;

DOI:10.1021/ja982125y

Reference yield:

triethylsilyl trifluoromethyl sulfonate (79271-56-0) → 5-((Z)-Hex-3-ene-1,5-diynyl)-3,6,6-trimethoxy-5-triethylsilanyloxy-cyclohexa-1,3-dienecarbaldehyde (204848-99-7)

Guidance literature:

Multi-step reaction with 3 steps

1: K₂CO₃, 2,6-lutidine / CH₂Cl₂ / 2 h / -78 °C

2: 18.6 g / DIBAL-H / toluene / 1.5 h / -78 °C

3: NaHCO₃, 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3-(1H)-one / CH₂Cl₂ / 0.5 h / 0 °C

With 2,6-dimethylpyridine; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; In dichloromethane; toluene;

DOI:10.1021/ja982125y

upstream raw materials:

[5-((Z)-Hex-3-ene-1,5-diynyl)-3,6,6-trimethoxy-5-triethylsilanyloxy-cyclohexa-1,3-dienyl]-methanol

triethylsilyl trifluoromethyl sulfonate

3-hydroxy-2,5-dimethoxybenzoic acid

3-bromo-2,5-dimethoxy-benzoic acid methyl ester

Refernces

• 1、 Churcher, Ian,Hallett, David,Magnus, Philip. "Synthesis of the antitumor agent aglycon (±)-calicheamicinone using an o-quinone monoketal strategy". . p. 10350 - 10358. Retrieved 2007/10/03.