methyl (2S,5'S)-2-(N-(benzyloxycarbonyl)amino)-3-(3-(methoxycarbonyl)-2-isoxazolidin-5-yl)propanoate

Base Information

• Chemical Name: methyl (2S,5'S)-2-(N-(benzyloxycarbonyl)amino)-3-(3-(methoxycarbonyl)-2-isoxazolidin-5-yl)propanoate
• CAS No.: 156426-52-7
• Molecular Formula: C₁₇H₂₀N₂O₇
• Molecular Weight: 364.355
• Mol file: 156426-52-7.mol

Synonyms:methyl (2S,5'S)-2-(N-(benzyloxycarbonyl)amino)-3-(3-(methoxycarbonyl)-2-isoxazolidin-5-yl)propanoate

Chemical Property of methyl (2S,5'S)-2-(N-(benzyloxycarbonyl)amino)-3-(3-(methoxycarbonyl)-2-isoxazolidin-5-yl)propanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2S,5'S)-2-(N-(benzyloxycarbonyl)amino)-3-(3-(methoxycarbonyl)-2-isoxazolidin-5-yl)propanoate

There total 4 articles about methyl (2S,5'S)-2-(N-(benzyloxycarbonyl)amino)-3-(3-(methoxycarbonyl)-2-isoxazolidin-5-yl)propanoate 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: 34.0%

methyl chlorooximidoacetate (30673-27-9) + methyl (2S)-2-[N-(benzyloxycarbonyl)amino]pent-4-enoate (78553-47-6) → methyl (2S)-2-(N-(benzyloxycarbonyl)amino)-3-(3-(methoxycarbonyl)-2-isoxazolin-4-yl)propanoate + methyl (2S,5'S)-2-(N-(benzyloxycarbonyl)amino)-3-(3-(methoxycarbonyl)-2-isoxazolidin-5-yl)propanoate (156426-52-7) + methyl (2S,5'R)-2-(N-(benzyloxycarbonyl)amino)-3-(3-(methoxycarbonyl)-2-isoxazolidin-5-yl)propanoate (156426-51-6)

Guidance literature:

With sodium carbonate; In diethyl ether; at 20 ℃; for 4h;

DOI:10.1021/ja00094a004

Reference yield:

L-allylglycine (16338-48-0) → methyl (2S,5'S)-2-(N-(benzyloxycarbonyl)amino)-3-(3-(methoxycarbonyl)-2-isoxazolidin-5-yl)propanoate (156426-52-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / HCl

2: 45 percent / Et₃N, 4-(N,N-dimethylamino)pyridine / CHCl₃ / 19 h / 20 °C

3: 39 percent / aq. Na₂CO₃ / diethyl ether / 4 h / 20 °C

With hydrogenchloride; dmap; sodium carbonate; triethylamine; In diethyl ether; chloroform;

DOI:10.1021/ja00094a004

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → methyl (2S,5'S)-2-(N-(benzyloxycarbonyl)amino)-3-(3-(methoxycarbonyl)-2-isoxazolidin-5-yl)propanoate (156426-52-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 45 percent / Et₃N, 4-(N,N-dimethylamino)pyridine / CHCl₃ / 19 h / 20 °C

2: 39 percent / aq. Na₂CO₃ / diethyl ether / 4 h / 20 °C

With dmap; sodium carbonate; triethylamine; In diethyl ether; chloroform;

DOI:10.1021/ja00094a004

upstream raw materials:

methyl chlorooximidoacetate

methyl (2S)-2-[N-(benzyloxycarbonyl)amino]pent-4-enoate

L-allylglycine

benzyl chloroformate

Downstream raw materials:

(2S,5'S)-2-amino-3-(3-carboxy-2-isoxazolin-5-yl)propanoic acid

(2S,5'S)-2-(N-(benzyloxycarbonyl)amino)-3-(3-carboxy-2-isoxazolin-5-yl)propanoic acid