(3S,4S)-3-benzyl-4-(N-benzyloxycarbonylamino)-butyrolactone

Base Information

• Chemical Name: (3S,4S)-3-benzyl-4-(N-benzyloxycarbonylamino)-butyrolactone
• CAS No.: 349148-55-6
• Molecular Formula: C₁₉H₁₉NO₄
• Molecular Weight: 325.364
• Mol file: 349148-55-6.mol

Synonyms:(3S,4S)-3-benzyl-4-(N-benzyloxycarbonylamino)-butyrolactone

Chemical Property of (3S,4S)-3-benzyl-4-(N-benzyloxycarbonylamino)-butyrolactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-3-benzyl-4-(N-benzyloxycarbonylamino)-butyrolactone

There total 1 articles about (3S,4S)-3-benzyl-4-(N-benzyloxycarbonylamino)-butyrolactone 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: 73.0%

benzyl (3S)-5-oxotetrahydro-3-furanylcarbamate (87219-29-2) + benzyl bromide (100-39-0) → (3S,4S)-3-benzyl-4-(N-benzyloxycarbonylamino)-butyrolactone (349148-55-6) + (3R,4S)-3-benzyl-4-(N-benzyloxycarbonylamino)-butyrolactone

Guidance literature:

benzyl (3S)-5-oxotetrahydro-3-furanylcarbamate; With lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -78 ℃; for 2h;

benzyl bromide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -78 ℃; for 3h;

DOI:10.1021/jo0014055

Reference yield: 87.0%

N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + (3S,4S)-3-benzyl-4-(N-benzyloxycarbonylamino)-butyrolactone (349148-55-6) → (2S,3S)-N-methoxy-N-methyl-2-benzyl-3-(benzyloxycarbonylamino)-4-hydroxybutanamide (349148-57-8)

Guidance literature:

With trimethylaluminum; In hexane; dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/jo0014055

Reference yield:

(3S,4S)-3-benzyl-4-(N-benzyloxycarbonylamino)-butyrolactone (349148-55-6) → 2-aziridin-2-yl-N-methoxy-N-methyl-3-phenyl-propionamide (349148-61-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / AlMe₃ / CH₂Cl₂; hexane / 1 h / 20 °C

2: 86 percent / PPh₃; DEAD / tetrahydrofuran / 3 h / 0 °C

3: H₂ / Pd/C / methanol / 2 h

With hydrogen; trimethylaluminum; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; 2: Intramolecular Mitsunobu reaction;

DOI:10.1021/jo0014055

upstream raw materials:

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

benzyl bromide

Downstream raw materials:

(2S,3S)-N-methoxy-N-methyl-2-benzyl-3-(benzyloxycarbonylamino)-4-hydroxybutanamide

2-aziridin-2-yl-N-methoxy-N-methyl-3-phenyl-propionamide

(2S,3S)-N-methoxy-N-methyl-2-benzyl-3,4-(benzyloxycarbonylimino)-butanamide

(S)-3-Phenyl-2-((S)-1-trityl-aziridin-2-yl)-propionaldehyde