(S)-2-benzyloxycarbonylamino-4-tert-butyldimethylsilyloxybutanpyrrolidinamide

Base Information

• Chemical Name: (S)-2-benzyloxycarbonylamino-4-tert-butyldimethylsilyloxybutanpyrrolidinamide
• CAS No.: 177839-61-1
• Molecular Formula: C₂₂H₃₆N₂O₄Si
• Molecular Weight: 420.624
• Mol file: 177839-61-1.mol

Synonyms:(S)-2-benzyloxycarbonylamino-4-tert-butyldimethylsilyloxybutanpyrrolidinamide

Chemical Property of (S)-2-benzyloxycarbonylamino-4-tert-butyldimethylsilyloxybutanpyrrolidinamide

Chemical Property:

Purity/Quality:

Safty Information:

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• Hazard Codes: 

MSDS Files:

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Technology Process of (S)-2-benzyloxycarbonylamino-4-tert-butyldimethylsilyloxybutanpyrrolidinamide

There total 4 articles about (S)-2-benzyloxycarbonylamino-4-tert-butyldimethylsilyloxybutanpyrrolidinamide 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:

benzyl (3S)-2-oxotetrahydro-3-furanylcarbamate (35677-89-5) → (S)-2-benzyloxycarbonylamino-4-tert-butyldimethylsilyloxybutanpyrrolidinamide (177839-61-1)

Guidance literature:

Multi-step reaction with 2 steps

1: AlMe₃ / CH₂Cl₂; hexane / 17 h / 25 °C

2: 3.24 g / imidazole / dimethylformamide / 17 h / 25 °C

With 1H-imidazole; trimethylaluminum; In hexane; dichloromethane; N,N-dimethyl-formamide; 1: Addition / 2: Condensation;

DOI:10.1021/jo991241w

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) + [(S)-3-Hydroxy-1-(pyrrolidine-1-carbonyl)-propyl]-carbamic acid benzyl ester → (S)-2-benzyloxycarbonylamino-4-tert-butyldimethylsilyloxybutanpyrrolidinamide (177839-61-1)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; Yield given;

DOI:10.1016/0040-4039(96)00518-7

Reference yield:

N-benzyloxycarbonyl-(L)-homoserine (35677-88-4) → (S)-2-benzyloxycarbonylamino-4-tert-butyldimethylsilyloxybutanpyrrolidinamide (177839-61-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 38.3 g / conc. HCl / ethanol

2: AlMe₃ / CH₂Cl₂; hexane / 17 h / 25 °C

3: 3.24 g / imidazole / dimethylformamide / 17 h / 25 °C

With 1H-imidazole; hydrogenchloride; trimethylaluminum; In ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; 1: Cyclization / 2: Addition / 3: Condensation;

DOI:10.1021/jo991241w

upstream raw materials:

tert-butyldimethylsilyl chloride

benzyl (3S)-2-oxotetrahydro-3-furanylcarbamate

N-benzyloxycarbonyl-(L)-homoserine

N-Benzyloxycarbonyl-L-asparaginsaeure-β-aethylester

Downstream raw materials:

(S)-2-benzyloxycarbonylamino-4-tert-butyldimethylsilyloxy-1-phenylbutan-1-one

[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzoyl)-propyl]-carbamic acid benzyl ester