(2R,3R)-allyl 3-methyl-1-(4-nitrobenzyloxycarbonyl)aziridine-2-carboxylate

Base Information

• Chemical Name: (2R,3R)-allyl 3-methyl-1-(4-nitrobenzyloxycarbonyl)aziridine-2-carboxylate
• CAS No.: 956283-76-4
• Molecular Formula: C₁₅H₁₆N₂O₆
• Molecular Weight: 320.302
• Mol file: 956283-76-4.mol

Synonyms:(2R,3R)-allyl 3-methyl-1-(4-nitrobenzyloxycarbonyl)aziridine-2-carboxylate

Chemical Property of (2R,3R)-allyl 3-methyl-1-(4-nitrobenzyloxycarbonyl)aziridine-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-allyl 3-methyl-1-(4-nitrobenzyloxycarbonyl)aziridine-2-carboxylate

There total 4 articles about (2R,3R)-allyl 3-methyl-1-(4-nitrobenzyloxycarbonyl)aziridine-2-carboxylate 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: 57.0%

(2R,3R)-allyl 3-methyl-1-tritylaziridine-2-carboxylate + 4-nitrobenzyl chloroformate (4457-32-3) → (2R,3R)-allyl 3-methyl-1-(4-nitrobenzyloxycarbonyl)aziridine-2-carboxylate (956283-76-4)

Guidance literature:

(2R,3R)-allyl 3-methyl-1-tritylaziridine-2-carboxylate; With trifluoroacetic acid; In methanol; dichloromethane; at 0 ℃; for 2h; Schlenk technique; Inert atmosphere;

4-nitrobenzyl chloroformate; With sodium carbonate; In diethyl ether; water; ethyl acetate; for 48h;

DOI:10.1021/acs.orglett.9b00125

Reference yield:

C7H11NO2 + 4-nitrobenzyl chloroformate (4457-32-3) → (2R,3R)-allyl 3-methyl-1-(4-nitrobenzyloxycarbonyl)aziridine-2-carboxylate (956283-76-4)

Guidance literature:

With sodium hydrogencarbonate; In water; ethyl acetate; at 20 ℃; for 24h;

DOI:10.1021/ol701742x

Reference yield:

H-D-Thr-Oallyl p-tolunenesulfonate → (2R,3R)-allyl 3-methyl-1-(4-nitrobenzyloxycarbonyl)aziridine-2-carboxylate (956283-76-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Schlenk technique; Inert atmosphere

1.2: 24 h / Schlenk technique; Inert atmosphere

2.1: triethylamine / tetrahydrofuran / 48 h / Reflux; Schlenk technique; Inert atmosphere

3.1: trifluoroacetic acid / dichloromethane; methanol / 2 h / 0 °C / Schlenk technique; Inert atmosphere

3.2: 48 h

With triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/acs.orglett.9b00125

upstream raw materials:

4-nitrobenzyl chloroformate

Refernces

• 1、 Liu, Hongqiang,Pattabiraman, Vijaya R.,Vederas, John C.. "Stereoselective syntheses of 4-oxa diaminopimelic acid and its protected derivatives via aziridine ring opening". . p. 4211 - 4214. Retrieved 2008/03/13.