methyl (2E,4S,5R)-4-acetoxy-2-(N-acetylamino)-5-((2S)-N-(benzyloxycarbonyl)aziridin-2-yl)-3-bromo-5-(p-methoxybenzyloxy)-2-pentenoate

Base Information

• Chemical Name: methyl (2E,4S,5R)-4-acetoxy-2-(N-acetylamino)-5-((2S)-N-(benzyloxycarbonyl)aziridin-2-yl)-3-bromo-5-(p-methoxybenzyloxy)-2-pentenoate
• CAS No.: 207679-31-0
• Molecular Formula: C₂₈H₃₁BrN₂O₉
• Molecular Weight: 619.466
• Mol file: 207679-31-0.mol

Synonyms:methyl (2E,4S,5R)-4-acetoxy-2-(N-acetylamino)-5-((2S)-N-(benzyloxycarbonyl)aziridin-2-yl)-3-bromo-5-(p-methoxybenzyloxy)-2-pentenoate

Chemical Property of methyl (2E,4S,5R)-4-acetoxy-2-(N-acetylamino)-5-((2S)-N-(benzyloxycarbonyl)aziridin-2-yl)-3-bromo-5-(p-methoxybenzyloxy)-2-pentenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2E,4S,5R)-4-acetoxy-2-(N-acetylamino)-5-((2S)-N-(benzyloxycarbonyl)aziridin-2-yl)-3-bromo-5-(p-methoxybenzyloxy)-2-pentenoate

There total 2 articles about methyl (2E,4S,5R)-4-acetoxy-2-(N-acetylamino)-5-((2S)-N-(benzyloxycarbonyl)aziridin-2-yl)-3-bromo-5-(p-methoxybenzyloxy)-2-pentenoate 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:

(S)-2-[(1R,2S)-2-Acetoxy-4-[(E)-acetylimino]-3-bromo-1-(4-methoxy-benzyloxy)-4-methoxycarbonyl-butyl]-aziridine-1-carboxylic acid benzyl ester → methyl (2Z,4S,5R)-4-acetoxy-2-(N-acetylamino)-5-((2S)-N-(benzyloxycarbonyl)aziridin-2-yl)-3-bromo-5-(p-methoxybenzyloxy)-2-pentenoate + methyl (2E,4S,5R)-4-acetoxy-2-(N-acetylamino)-5-((2S)-N-(benzyloxycarbonyl)aziridin-2-yl)-3-bromo-5-(p-methoxybenzyloxy)-2-pentenoate (207679-31-0)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine; In dichloromethane; at 25 ℃; for 8h;

DOI:10.1007/BF02317807

Reference yield:

(S)-2-[(Z)-(1R,2R)-2-Acetoxy-4-acetylamino-1-(4-methoxy-benzyloxy)-4-methoxycarbonyl-but-3-enyl]-aziridine-1-carboxylic acid benzyl ester (207679-30-9) → methyl (2E,4S,5R)-4-acetoxy-2-(N-acetylamino)-5-((2S)-N-(benzyloxycarbonyl)aziridin-2-yl)-3-bromo-5-(p-methoxybenzyloxy)-2-pentenoate (207679-31-0)

Guidance literature:

Multi-step reaction with 2 steps

1: N-bromosuccinimide / CH₂Cl₂ / 4 h / 25 °C

2: 2,2,6,6-tetramethylpiperidine / CH₂Cl₂ / 8 h / 25 °C

With 2,2,6,6-tetramethyl-piperidine; N-Bromosuccinimide; In dichloromethane; 1: Bromination / 2: Rearrangement;

DOI:10.1007/BF02317807

Reference yield:

methyl (2E,4S,5R)-4-acetoxy-2-(N-acetylamino)-5-((2S)-N-(benzyloxycarbonyl)aziridin-2-yl)-3-bromo-5-(p-methoxybenzyloxy)-2-pentenoate (207679-31-0) → (E)-(4S,5R)-4-Acetoxy-2-acetylamino-5-(S)-aziridin-2-yl-3-bromo-5-(4-methoxy-benzyloxy)-pent-2-enoic acid methyl ester (208396-50-3)

Guidance literature:

With triethylsilane; triethylamine; palladium diacetate; In dichloromethane; at 25 ℃;

DOI:10.1007/BF02317807

upstream raw materials:

(S)-2-[(Z)-(1R,2R)-2-Acetoxy-4-acetylamino-1-(4-methoxy-benzyloxy)-4-methoxycarbonyl-but-3-enyl]-aziridine-1-carboxylic acid benzyl ester

Downstream raw materials:

(E)-(4S,5R)-4-Acetoxy-2-acetylamino-5-(S)-aziridin-2-yl-3-bromo-5-(4-methoxy-benzyloxy)-pent-2-enoic acid methyl ester