1-BENZYL 2-METHYL (S)-(-)-1,2-AZIRIDINEDICARBOXYLATE

Base Information

• Chemical Name: 1-BENZYL 2-METHYL (S)-(-)-1,2-AZIRIDINEDICARBOXYLATE
• CAS No.: 104597-98-0
• Molecular Formula: C12H13 N O4
• Molecular Weight: 235.24
• Hs Code.: 2933990090
• Mol file: 104597-98-0.mol

Synonyms:1,2-Aziridinedicarboxylicacid, 2-methyl 1-(phenylmethyl) ester, (S)-; (2S)-1,2-Aziridinedicarboxylicacid 2-methyl 1-(phenylmethyl) ester; (S)-N-Cbz-aziridine-2-carboxylic acidmethyl ester; (S)-N-[(Benzyloxy)carbonyl]aziridine-2-carboxylic acid methylester; Methyl (S)-1-(benzyloxycarbonyl)aziridine-2-carboxylate; Methyl(S)-N-Cbz-aziridine-2-carboxylate; Methyl(S)-N-[(benzyloxy)carbonyl]aziridine-2-carboxylate

Chemical Property of 1-BENZYL 2-METHYL (S)-(-)-1,2-AZIRIDINEDICARBOXYLATE

Chemical Property:

• Vapor Pressure: 7.04E-05mmHg at 25°C
• Refractive Index: n20/D 1.519(lit.)
• Boiling Point: 343.4°Cat760mmHg
• PKA: -5.65±0.40(Predicted)
• Flash Point: 161.5°C
• PSA: 55.61000
• Density: 1.305g/cm³
• LogP: 1.11830
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Soluble), Dichloromethane

Purity/Quality:

99% ^*data from raw suppliers

(S)-N-[(Benzyloxy)carbonyl]aziridine-2-carboxylicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Methyl (S)-(–)-N-Z-aziridine-2-carboxylate is a chiral building block that is commonly used in the organic stereoselective synthesis of various compounds, including anticancer agents, antibiotics, and enzyme inhibitors.
• Uses: Like aziridine carboxylic acid ester derivative, (S)-1-Benzyl 2-methyl aziridine-1,2-dicarboxylate can be used for the synthetic application of chiral aziridine via esterification.

Technology Process of 1-BENZYL 2-METHYL (S)-(-)-1,2-AZIRIDINEDICARBOXYLATE

There total 5 articles about 1-BENZYL 2-METHYL (S)-(-)-1,2-AZIRIDINEDICARBOXYLATE 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: 96.0%

benzyl chloroformate (501-53-1,94274-21-2) + methyl (2S)-N-tritylaziridine-2-carboxylate (75154-68-6) → (S)-2-methoxycarbonyl-1-benzyloxycarbonylaziridine (104597-98-0)

Guidance literature:

methyl (2S)-N-tritylaziridine-2-carboxylate; With trifluoroacetic acid; In methanol; chloroform; at 0 ℃; for 4h;

benzyl chloroformate; In water; ethyl acetate; at 20 ℃; for 20h;

DOI:10.1039/b508199h

Reference yield: 78.0%

methanol (67-56-1) + (4R,7S)-1-[{(2'S)-(1'-benzyloxycarbonyl)aziridin-2'-yl}carbonyl]-7-isopropyl-4-methyl-3-phenyl-4,5,6,7-tetrahydro-1H-indazole (1314042-77-7) → (S)-2-methoxycarbonyl-1-benzyloxycarbonylaziridine (104597-98-0) + (4R,7S)-3-phenyl-4-methyl-7-isopropyl-4,5,6,7-tetrahydro-1H-indazole (155095-10-6)

Guidance literature:

With dmap; at 20 ℃; for 5h; Inert atmosphere;

DOI:10.1021/jo2010632

Reference yield: 35.0%

methanol (67-56-1) + O-p-toluenesulfonyl benzyloxyhydroxamate (64420-86-6) + acrolein (107-02-8,25068-14-8) → (S)-2-methoxycarbonyl-1-benzyloxycarbonylaziridine (104597-98-0)

Guidance literature:

O-p-toluenesulfonyl benzyloxyhydroxamate; acrolein; With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; sodium acetate; In chloroform; at 20 ℃;

methanol; With sodium cyanide; manganese(IV) oxide; at 0 ℃; for 0.666667h; optical yield given as %ee; enantioselective reaction;

DOI:10.1002/chem.201100042

upstream raw materials:

benzyl chloroformate

methyl (2S)-N-tritylaziridine-2-carboxylate

(S)-methyl aziridine-2-carboxylate

methanol

Downstream raw materials:

(S)-2-Benzyloxycarbonylamino-3-(5-methoxy-1H-indol-3-yl)-propionic acid methyl ester

(2S)-2-(benzyloxycarbonylamino)-3-(1,1-dimethylallyloxy)propionic acid methyl ester

methyl (2R)-N-carbobenzyloxy-β-hydroxyethylcysteineate

(S)-methyl 2-(((benzyloxy)carbonyl)amino)-3-isopropoxypropanoate

Refernces

• 1、 -. "IMMUNOPROTEASOME INHIBITORS". Paragraph 0276. . Retrieved 2019/06/13.
• 2、 Deiana, Luca,Dziedzic, Pawel,Zhao, Gui-Ling,Vesely, Jan,Ibrahem, Ismail,Rios, Ramon,Sun, Junliang,Cordova, Armando. "Catalytic asymmetric aziridination of α,β-unsaturated aldehydes". supporting information; experimental part. p. 7904 - 7917. Retrieved 2011/08/05.