(4S,5S)-5-(2-((tert-butyldimethylsilyl)oxy)ethyl)-4-((triisopropylsilyl)oxy)cyclopent-2-enone

Base Information

• Chemical Name: (4S,5S)-5-(2-((tert-butyldimethylsilyl)oxy)ethyl)-4-((triisopropylsilyl)oxy)cyclopent-2-enone
• CAS No.: 1591271-03-2
• Molecular Formula: C₂₂H₄₄O₃Si₂
• Molecular Weight: 412.761

Synonyms:(4S,5S)-5-(2-((tert-butyldimethylsilyl)oxy)ethyl)-4-((triisopropylsilyl)oxy)cyclopent-2-enone

Chemical Property of (4S,5S)-5-(2-((tert-butyldimethylsilyl)oxy)ethyl)-4-((triisopropylsilyl)oxy)cyclopent-2-enone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-5-(2-((tert-butyldimethylsilyl)oxy)ethyl)-4-((triisopropylsilyl)oxy)cyclopent-2-enone

There total 1 articles about (4S,5S)-5-(2-((tert-butyldimethylsilyl)oxy)ethyl)-4-((triisopropylsilyl)oxy)cyclopent-2-enone 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:

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → (4S,5S)-5-(2-((tert-butyldimethylsilyl)oxy)ethyl)-4-((triisopropylsilyl)oxy)cyclopent-2-enone (1591271-03-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 14 h / 0 °C / Inert atmosphere

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 1 h / Inert atmosphere; Reflux

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 3.5 h / 0 °C / Inert atmosphere

4.1: 1H-imidazole / Inert atmosphere

4.2: Inert atmosphere

With 1H-imidazole; 2,6-dimethylpyridine; lithium aluminium tetrahydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane;

DOI:10.1002/ejoc.201301616

Reference yield:

(4S,5S)-5-(2-((tert-butyldimethylsilyl)oxy)ethyl)-4-((triisopropylsilyl)oxy)cyclopent-2-enone (1591271-03-2) → triisopropyl(((4S,5R,6S,7S,8R)-4-((S)-1-((4-methoxybenzyl)oxy)propan-2-yl)-6-(2-((2-methoxypropan-2-yl)oxy)ethyl)-2,2,8-trimethyl-1,3-dioxaspiro[4.4]nonan-7-yl)oxy)silane (1591271-15-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: copper(l) iodide / diethyl ether / 1 h / -78 - 0 °C / Inert atmosphere

1.2: 1 h / -78 °C / Inert atmosphere

2.1: tert.-butyl lithium / pentane; diethyl ether / 0.58 h / -78 - 20 °C / Inert atmosphere

2.2: 5 h / -78 °C / Inert atmosphere

3.1: pyridine; ozone; Sudan III / methanol; dichloromethane / -78 °C / Inert atmosphere

3.2: 12 h / 20 °C / Inert atmosphere

4.1: sodium tetrahydroborate / dichloromethane; ethanol / 24 h / 20 °C / Inert atmosphere

5.1: pyridinium p-toluenesulfonate / 24 h / 20 °C / Inert atmosphere

With pyridine; sodium tetrahydroborate; copper(l) iodide; tert.-butyl lithium; pyridinium p-toluenesulfonate; ozone; Sudan III; In methanol; diethyl ether; ethanol; dichloromethane; pentane;

DOI:10.1002/ejoc.201301616

Reference yield:

(4S,5S)-5-(2-((tert-butyldimethylsilyl)oxy)ethyl)-4-((triisopropylsilyl)oxy)cyclopent-2-enone (1591271-03-2) → triisopropyl(((4S,5R,6S,7S,8R)-4-((S)-1-((4-methoxybenzyl)oxy)propan-2-yl)-6-(2-((2-methoxypropan-2-yl)oxy)ethyl)-2,2,8-trimethyl-1,3-dioxaspiro[4.4]nonan-7-yl)oxy)silane

Guidance literature:

Multi-step reaction with 5 steps

1.1: copper(l) iodide / diethyl ether / 1 h / -78 - 0 °C / Inert atmosphere

1.2: 1 h / -78 °C / Inert atmosphere

2.1: tert.-butyl lithium / pentane; diethyl ether / 0.58 h / -78 - 20 °C / Inert atmosphere

2.2: 5 h / -78 °C / Inert atmosphere

3.1: pyridine; ozone; Sudan III / methanol; dichloromethane / -78 °C / Inert atmosphere

3.2: 12 h / 20 °C / Inert atmosphere

4.1: sodium tetrahydroborate / dichloromethane; ethanol / 24 h / 20 °C / Inert atmosphere

5.1: pyridinium p-toluenesulfonate / 3 h / 20 °C / Inert atmosphere

With pyridine; sodium tetrahydroborate; copper(l) iodide; tert.-butyl lithium; pyridinium p-toluenesulfonate; ozone; Sudan III; In methanol; diethyl ether; ethanol; dichloromethane; pentane;

DOI:10.1002/ejoc.201301616

upstream raw materials:

triisopropylsilyl trifluoromethanesulfonate

Downstream raw materials:

(1R,2S,3S,4R)-2-(2-((tert-butyldimethylsilyl)oxy)ethyl)-1-((R)-4-((4-methoxybenzyl)oxy)-3-methylbut-1-en-2-yl)-4-methyl-3-((triisopropylsilyl)oxy)cyclopentan-1-ol

(1S,2S,3S,4R)-2-(2-((tert-butyldimethylsilyl)oxy)ethyl)-1-((R)-4-((4-methoxybenzyl)oxy)-3-methylbut-1-en-2-yl)-4-methyl-3-((triisopropylsilyl)oxy)cyclopentan-1-ol

(1R,2S,3S,4R)-2-(2-((tert-butyldimethylsilyl)oxy)ethyl)-1-((1S,2S)-1-hydroxy-3-((4-methoxybenzyl)oxy)-2-methylpropyl)-4-methyl-3-((triisopropylsilyl)oxy)cyclopentan-1-ol

(1R,2S,3S,4R)-2-(2-((tert-butyldimethylsilyl)oxy)ethyl)-1-((1R,2S)-1-hydroxy-3-((4-methoxybenzyl)oxy)-2-methylpropyl)-4-methyl-3-((triisopropylsilyl)oxy)cyclopentan-1-ol

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