(3S)-3-benzyloxycarbonylamino-2-ethyl-γ-butirolactone

Base Information

• Chemical Name: (3S)-3-benzyloxycarbonylamino-2-ethyl-γ-butirolactone
• CAS No.: 112346-94-8
• Molecular Formula: C₁₄H₁₇NO₄
• Molecular Weight: 263.293
• Mol file: 112346-94-8.mol

Synonyms:

Chemical Property of (3S)-3-benzyloxycarbonylamino-2-ethyl-γ-butirolactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S)-3-benzyloxycarbonylamino-2-ethyl-γ-butirolactone

There total 3 articles about (3S)-3-benzyloxycarbonylamino-2-ethyl-γ-butirolactone 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:

N-Cbz-L-Asp (1152-61-0) → (3S)-3-benzyloxycarbonylamino-2-ethyl-γ-butirolactone (94718-14-6,112346-94-8,112346-95-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / thionyl chloride / ethyl acetate / 1 h / Ambient temperature

2: 1.) sodium borohydride; 2.) HCl / 1.) THF, 0 deg C, 15 min, r.t. 1 h; 2.) EtOH, reflux 1,5 h

3: 1.) LDA; 2.) HMPT / 1.) THF, -78 deg C; 2.) -78 - 0 deg C, 1 h

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; thionyl chloride; lithium diisopropyl amide; In ethyl acetate;

DOI:10.1248/cpb.34.3020

Reference yield:

N-benzyloxycarbonyl-L-aspartic acid anhydride (4515-23-5) → (3S)-3-benzyloxycarbonylamino-2-ethyl-γ-butirolactone (94718-14-6,112346-94-8,112346-95-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) sodium borohydride; 2.) HCl / 1.) THF, 0 deg C, 15 min, r.t. 1 h; 2.) EtOH, reflux 1,5 h

2: 1.) LDA; 2.) HMPT / 1.) THF, -78 deg C; 2.) -78 - 0 deg C, 1 h

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; lithium diisopropyl amide;

DOI:10.1248/cpb.34.3020

Reference yield:

benzyl (3S)-5-oxotetrahydro-3-furanylcarbamate (87219-29-2) + ethyl iodide (75-03-6) → (3S)-3-benzyloxycarbonylamino-2-ethyl-γ-butirolactone (94718-14-6,112346-94-8,112346-95-9) + (3S)-3-benzyloxycarbonylamino-2-diethyl-γ-butirolactone (94718-15-7)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide; Yield given. Multistep reaction. Yields of byproduct given; 1.) THF, -78 deg C; 2.) -78 - 0 deg C, 1 h;

DOI:10.1248/cpb.34.3020

upstream raw materials:

benzyl (3S)-5-oxotetrahydro-3-furanylcarbamate

ethyl iodide

N-Cbz-L-Asp

N-benzyloxycarbonyl-L-aspartic acid anhydride

Downstream raw materials:

(3S)-2-ethyl-3-benzyloxycarbonylamino-4-(tert-butyldimethyl-silyloxy)butanoic acid

(S)-3-Benzyloxycarbonylamino-2-ethyl-4-hydroxy-butyric acid