erythro, threo-DL-N-benzyloxycarbonyl-α-amino-2-(p-methoxybenzyl)-3-oxo-5-isoxazolidineacetic acid o-nitrobenzyl ester

Base Information

• Chemical Name: erythro, threo-DL-N-benzyloxycarbonyl-α-amino-2-(p-methoxybenzyl)-3-oxo-5-isoxazolidineacetic acid o-nitrobenzyl ester
• CAS No.: 104754-70-3
• Molecular Formula: C₂₈H₂₇N₃O₉
• Molecular Weight: 549.537
• Mol file: 104754-70-3.mol

Synonyms:

Chemical Property of erythro, threo-DL-N-benzyloxycarbonyl-α-amino-2-(p-methoxybenzyl)-3-oxo-5-isoxazolidineacetic acid o-nitrobenzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of erythro, threo-DL-N-benzyloxycarbonyl-α-amino-2-(p-methoxybenzyl)-3-oxo-5-isoxazolidineacetic acid o-nitrobenzyl ester

There total 12 articles about erythro, threo-DL-N-benzyloxycarbonyl-α-amino-2-(p-methoxybenzyl)-3-oxo-5-isoxazolidineacetic acid o-nitrobenzyl ester 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: 95.0%

N-benzyloxycarbonyl-α-(o-nitrobenzyl)-(Z)-α,β-dehydroglutanic-γ-(N-p-methoxybenzyl)hydroxamic acid (104754-69-0) → erythro, threo-DL-N-benzyloxycarbonyl-α-amino-2-(p-methoxybenzyl)-3-oxo-5-isoxazolidineacetic acid o-nitrobenzyl ester (104754-70-3,104760-95-4)

Guidance literature:

With sodium hydrogencarbonate; for 0.666667h; Heating;

DOI:10.1016/S0040-4020(01)96774-2

Reference yield:

p-methoxyl benzaldoxime (3717-21-3,3717-22-4,140461-28-5,140461-29-6,3235-04-9) → erythro, threo-DL-N-benzyloxycarbonyl-α-amino-2-(p-methoxybenzyl)-3-oxo-5-isoxazolidineacetic acid o-nitrobenzyl ester (104754-70-3,104760-95-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) NaBH₃CN, 2.) imidazole / 1.) MeOH, pH 3, 2.) DMF

2: 1.) DCC, N-hydroxysuccinimide, 2.) anhydrous KF / 1.) THF, 2.) EtOH

3: NaHCO₃ / H₂O

With 1H-imidazole; potassium fluoride; 1-hydroxy-pyrrolidine-2,5-dione; sodium cyanoborohydride; sodium hydrogencarbonate; dicyclohexyl-carbodiimide; In water;

DOI:10.1021/ja00394a039

Reference yield:

O-(t-butyldimethylsilyl)-N-(p-methoxybenzyl)-hydroxylamine (76843-80-6) → erythro, threo-DL-N-benzyloxycarbonyl-α-amino-2-(p-methoxybenzyl)-3-oxo-5-isoxazolidineacetic acid o-nitrobenzyl ester (104754-70-3,104760-95-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) DCC, N-hydroxysuccinimide, 2.) anhydrous KF / 1.) THF, 2.) EtOH

2: NaHCO₃ / H₂O

With potassium fluoride; 1-hydroxy-pyrrolidine-2,5-dione; sodium hydrogencarbonate; dicyclohexyl-carbodiimide; In water;

DOI:10.1021/ja00394a039

upstream raw materials:

N-benzyloxycarbonyl-α-(o-nitrobenzyl)-(Z)-α,β-dehydroglutanic-γ-(N-p-methoxybenzyl)hydroxamic acid

p-methoxyl benzaldoxime

O-(t-butyldimethylsilyl)-N-(p-methoxybenzyl)-hydroxylamine

α-ketoglutaric acid

Downstream raw materials:

erythro-DL-N-benzyloxycarbonyl-α-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid

threo-DL-N-benzyloxycarbonyl-α-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid o-nitrobenzyl ester

erythro-DL-N-benzyloxycarbonyl-α-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid o-nitrobenzyl ester