1-Azaspiro[5.5]undecan-7-one, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-hydroxy-1-[(4-methylphenyl)sulf onyl]-, (3S,5S,6R)-

Base Information

• Chemical Name: 1-Azaspiro[5.5]undecan-7-one, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-hydroxy-1-[(4-methylphenyl)sulf onyl]-, (3S,5S,6R)-
• CAS No.: 353248-28-9
• Molecular Formula: C23H37NO5SSi
• Molecular Weight: 467.702
• Mol file: 353248-28-9.mol

Synonyms:

Chemical Property of 1-Azaspiro[5.5]undecan-7-one, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-hydroxy-1-[(4-methylphenyl)sulf onyl]-, (3S,5S,6R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-Azaspiro[5.5]undecan-7-one, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-hydroxy-1-[(4-methylphenyl)sulf onyl]-, (3S,5S,6R)-

There total 5 articles about 1-Azaspiro[5.5]undecan-7-one, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-hydroxy-1-[(4-methylphenyl)sulf onyl]-, (3S,5S,6R)- 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: 96.0%

(-)-(1R,4S,7S)-4-(tert-butyldimethylsilanyloxy)-2-(toluene-4-sulfonyl)-1-(1-trimethylsilanyloxycyclopentyl)-7-oxa-2-azabicyclo[4.1.0]heptane (353248-27-8) → (-)-(3S,5S,6R)-3-(tert-butyldimethylsilanyloxy)-5-hydroxy-1-(toluene-4-sulfonyl)-1-azaspiro[5.5]undecan-7-one (353248-28-9)

Guidance literature:

With titanium tetrachloride; In dichloromethane; at -78 ℃; for 0.5h;

DOI:10.1021/ol035566h

Reference yield:

(+)-1-[(5S)-5-(tert-butyldimethylsilanyloxy)-1-(toluene-4-sulfonyl)-1,4,5,6-tetrahydropyridin-2-yl]cyclopentanol (353248-25-6) → (-)-(3S,5S,6R)-3-(tert-butyldimethylsilanyloxy)-5-hydroxy-1-(toluene-4-sulfonyl)-1-azaspiro[5.5]undecan-7-one (353248-28-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: K₂CO₃; dimethyldioxirane / acetone

1.2: 83 percent / 2,6-lutidine / tetrahydrofuran / 0.25 h / 20 °C

2.1: 96 percent / TiCl₄ / CH₂Cl₂ / 0.5 h / -78 °C

With 3,3-dimethyldioxirane; potassium carbonate; titanium tetrachloride; In dichloromethane; acetone;

DOI:10.1021/jo049356+

Reference yield:

(+)-(3S)-3-(tert-butyldimethylsilanyloxy)-1-(toluene-4-sulfonyl)-6-trimethylstannyl-1,2,3,4-tetrahydropyridine → (-)-(3S,5S,6R)-3-(tert-butyldimethylsilanyloxy)-5-hydroxy-1-(toluene-4-sulfonyl)-1-azaspiro[5.5]undecan-7-one (353248-28-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: MeLi / diethyl ether / 0.17 h / 0 °C

1.2: MgBr₂ / diethyl ether / 0.5 h / -78 °C

1.3: 89 percent / diethyl ether / -100 - 20 °C

2.1: K₂CO₃; dimethyldioxirane / acetone

2.2: 83 percent / 2,6-lutidine / tetrahydrofuran / 0.25 h / 20 °C

3.1: 96 percent / TiCl₄ / CH₂Cl₂ / 0.5 h / -78 °C

With methyllithium; 3,3-dimethyldioxirane; potassium carbonate; titanium tetrachloride; In diethyl ether; dichloromethane; acetone;

DOI:10.1021/jo049356+

upstream raw materials:

(-)-(1R,4S,7S)-4-(tert-butyldimethylsilanyloxy)-2-(toluene-4-sulfonyl)-1-(1-trimethylsilanyloxycyclopentyl)-7-oxa-2-azabicyclo[4.1.0]heptane

1-[(1R,4S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(toluene-4-sulfonyl)-7-oxa-2-aza-bicyclo[4.1.0]hept-1-yl]-cyclopentanol

(+)-1-[(5S)-5-(tert-butyldimethylsilanyloxy)-1-(toluene-4-sulfonyl)-1,4,5,6-tetrahydropyridin-2-yl]cyclopentanol

Downstream raw materials:

(+)-(3S,6R)-3-(tert-butyldimethylsilanyloxy)-1-(toluene-4-sulfonyl)-1-azaspiro[5.5]undec-4-en-7-one

(-)-(3S,5S,6R)-methanesulfonic acid 3-(tert-butyldimethylsilanyloxy)-7-oxo-1-(toluene-4-sulfonyl)-1-azaspiro[5.5]undec-5-yl ester