(αS,3S)-3-[[(1,1-dimethylethoxy)carbonyl]methylamino]-α-[(4-methoxyphenyl)methyl]-2,8-dioxo-1-azaspiro[4,5]decane-1-acetaldehyde

Base Information

• Chemical Name: (αS,3S)-3-[[(1,1-dimethylethoxy)carbonyl]methylamino]-α-[(4-methoxyphenyl)methyl]-2,8-dioxo-1-azaspiro[4,5]decane-1-acetaldehyde
• CAS No.: 248948-53-0
• Molecular Formula: C₂₅H₃₄N₂O₆
• Molecular Weight: 458.555
• Mol file: 248948-53-0.mol

Synonyms:(αS,3S)-3-[[(1,1-dimethylethoxy)carbonyl]methylamino]-α-[(4-methoxyphenyl)methyl]-2,8-dioxo-1-azaspiro[4,5]decane-1-acetaldehyde

Chemical Property of (αS,3S)-3-[[(1,1-dimethylethoxy)carbonyl]methylamino]-α-[(4-methoxyphenyl)methyl]-2,8-dioxo-1-azaspiro[4,5]decane-1-acetaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (αS,3S)-3-[[(1,1-dimethylethoxy)carbonyl]methylamino]-α-[(4-methoxyphenyl)methyl]-2,8-dioxo-1-azaspiro[4,5]decane-1-acetaldehyde

There total 9 articles about (αS,3S)-3-[[(1,1-dimethylethoxy)carbonyl]methylamino]-α-[(4-methoxyphenyl)methyl]-2,8-dioxo-1-azaspiro[4,5]decane-1-acetaldehyde 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:

(αS,3S)-3-[[(1,1-dimethylethoxy)carbonyl]methylamino]-1-[2-hydroxy-1-[(4-methoxyphenyl)methyl]ethyl]-1-azaspiro[4,5]decane-2,8-dione (248948-51-8) → (αS,3S)-3-[[(1,1-dimethylethoxy)carbonyl]methylamino]-α-[(4-methoxyphenyl)methyl]-2,8-dioxo-1-azaspiro[4,5]decane-1-acetaldehyde (248948-53-0)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 25 ℃; for 0.5h;

DOI:10.1021/ja991160h

Reference yield:

(S)-2-(11-Hydroxy-10-oxo-1,4-dioxa-9-aza-dispiro[4.2.4.2]tetradec-9-yl)-3-(4-methoxy-phenyl)-propionic acid methyl ester → (αS,3S)-3-[[(1,1-dimethylethoxy)carbonyl]methylamino]-α-[(4-methoxyphenyl)methyl]-2,8-dioxo-1-azaspiro[4,5]decane-1-acetaldehyde (248948-53-0)

Guidance literature:

Multi-step reaction with 8 steps

1: DMAP / CH₂Cl₂ / 12 h / 25 °C

2: NaN₃ / dimethylformamide / 12 h / 25 °C

3: 90 percent / H₂ / 5 percent Pd/C / ethanol / 760 Torr

4: 92 percent / NaH / dimethylformamide / 2 h / 25 °C

5: LiBH₄ / diethyl ether / 2 h

6: aq. HCl / acetic acid / 12 h

7: 95 percent / Et₃N / CH₂Cl₂ / 3 h / 25 °C

8: Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 25 °C

With hydrogenchloride; dmap; lithium borohydride; sodium azide; hydrogen; sodium hydride; Dess-Martin periodane; triethylamine; palladium on activated charcoal; In diethyl ether; ethanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; 1: Tosylation / 2: Substitution / 3: Hydrogenolysis / 4: Methylation / 5: Reduction / 6: Hydrolysis / 7: Acylation / 8: Oxidation;

DOI:10.1021/ja991160h

Reference yield:

methyl (αS,3S)-11-azido-α-[(4-methoxyphenyl)methyl]-10-oxo-1,4-dioxa-9-azadispiro[4.2.4.2]tetradecane-9-acetate (248948-40-5) → (αS,3S)-3-[[(1,1-dimethylethoxy)carbonyl]methylamino]-α-[(4-methoxyphenyl)methyl]-2,8-dioxo-1-azaspiro[4,5]decane-1-acetaldehyde (248948-53-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 90 percent / H₂ / 5 percent Pd/C / ethanol / 760 Torr

2: 92 percent / NaH / dimethylformamide / 2 h / 25 °C

3: LiBH₄ / diethyl ether / 2 h

4: aq. HCl / acetic acid / 12 h

5: 95 percent / Et₃N / CH₂Cl₂ / 3 h / 25 °C

6: Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 25 °C

With hydrogenchloride; lithium borohydride; hydrogen; sodium hydride; Dess-Martin periodane; triethylamine; palladium on activated charcoal; In diethyl ether; ethanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; 1: Hydrogenolysis / 2: Methylation / 3: Reduction / 4: Hydrolysis / 5: Acylation / 6: Oxidation;

DOI:10.1021/ja991160h

upstream raw materials:

(αS,3S)-3-[[(1,1-dimethylethoxy)carbonyl]methylamino]-1-[2-hydroxy-1-[(4-methoxyphenyl)methyl]ethyl]-1-azaspiro[4,5]decane-2,8-dione

di-tert-butyl dicarbonate

(αS,3S)-1-[2-hydroxy-1-[(4-methoxyphenyl)methyl]ethyl]-3-methylamino-1-azaspiro[4,5]decane-2,8-dione

methyl (αS,3S)-11-azido-α-[(4-methoxyphenyl)methyl]-10-oxo-1,4-dioxa-9-azadispiro[4.2.4.2]tetradecane-9-acetate

Downstream raw materials:

(2S,5S,6S,7R,8R,10aS)-2-[[(benzyloxy)carbonyl]methylamino]-6-(triethylsilyloxy)octahydro-5-[(4-methoxyphenyl)methyl]-1H-7,10a-methanopyrrolo[1,2-a]azocin-8-yl (4-nitrobenzene)sulfonate

(2S,5S,6S,7R,8S,10aS)-2-[[(benzyloxy)carbonyl]methylamino]-6-(triethylsilyloxy)octahydro-5-[(4-methoxyphenyl)methyl]-1H-7,10a-methanopyrrolo[1,2-a]azocin-8-yl dibenzyl phosphate

(2S,5S,6S,7R,8S,10aS)-2-[[(benzyloxy)carbonyl]methylamino]octahydro-6-hydroxy-5-[(4-methoxyphenyl)methyl]-1H-7,10a-methanopyrrolo[1,2-a]azocin-8-yl dibenzyl phosphate

(2S,5S,6S,7R,8R,10aS)-2-[[(benzyloxy)carbonyl]methylamino]octahydro-6-hydroxy-5-[(4-methoxyphenyl)methyl]-1H-7,10a-methanopyrrolo[1,2-a]azocin-8-yl (4-nitrobenzene)sulfonate