1-Benzyl 2-methyl (S)-(-)-1,2-aziridinedicarboxylate

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1-Benzyl 2-methyl (S)-(-)-1,2-aziridinedicarboxylate Basic information
Product Name:1-Benzyl 2-methyl (S)-(-)-1,2-aziridinedicarboxylate
Synonyms:(S)-1-benzyl 2-methyl aziridine-1,2-dicarboxylate;Methyl (S)-(-)-N-Z-aziridine-2-carboxylate;Methyl (S)-(-)-N-benzyloxycarbonylaziridine-2-carboxylate;aziridine-1,2-dicarboxylic acid O2-methyl ester O1-(phenylmethyl) ester;Methyl (S)-(-)-N-Z-aziridine-2-carboxylate 96%;1,2-Aziridinedicarboxylic acid, 2-methyl 1-(phenylmethyl) ester, (2S)-;Methyl (S)-1-Cbz-aziridine-2-carboxylate;1-O-benzyl 2-O-methyl (2S)-aziridine-1,2-dicarboxylate
CAS:104597-98-0
MF:C12H13NO4
MW:235.24
EINECS:
Product Categories:Aziridines;Chiral Building Blocks;Organic Building Blocks
Mol File:104597-98-0.mol
1-Benzyl 2-methyl (S)-(-)-1,2-aziridinedicarboxylate Structure
1-Benzyl 2-methyl (S)-(-)-1,2-aziridinedicarboxylate Chemical Properties
Boiling point 160-165 °C/2 mmHg (lit.)
density 1.19 g/mL at 25 °C (lit.)
refractive index n20/D 1.519(lit.)
Fp 110 °C
storage temp. Sealed in dry,Store in freezer, under -20°C
solubility Chloroform (Slightly), DMSO (Slightly), Methanol (Soluble), Dichloromethane
form Oil
pka-5.65±0.40(Predicted)
color Colourless
Optical Rotation[α]20/D 25°, c = 1 in toluene
InChIInChI=1S/C12H13NO4/c1-16-11(14)10-7-13(10)12(15)17-8-9-5-3-2-4-6-9/h2-6,10H,7-8H2,1H3/t10-,13/m0/s1
InChIKeyGTZJUBQWCWZING-NKUHCKNESA-N
SMILESN1(C(OCC2=CC=CC=C2)=O)C[C@H]1C(OC)=O
Safety Information
WGK Germany 3
Storage Class10 - Combustible liquids
MSDS Information
1-Benzyl 2-methyl (S)-(-)-1,2-aziridinedicarboxylate Usage And Synthesis
DescriptionMethyl (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.
UsesLike 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.
References[1] YUEXIAN LI . Synthesis of potent BCRP inhibitor—Ko143[J]. Tetrahedron Letters, 2008, 49 9: Pages 1480-1483. DOI: 10.1016/j.tetlet.2007.12.130
[2] FRANCESCA BARTOCCINI. Total Synthesis of ()-Clavicipitic Acid via γ,γ-Dimethylallyltryptophan (DMAT) and Chemoselective C–H Hydroxylation[J]. The Journal of Organic Chemistry, 2019, 84 12: 8027-8034. DOI: 10.1021/acs.joc.9b00879
1-Benzyl 2-methyl (S)-(-)-1,2-aziridinedicarboxylate Preparation Products And Raw materials
Preparation ProductsN-(Benzyloxycarbonyl)-L--chloroalanine Methyl Ester
Tag:1-Benzyl 2-methyl (S)-(-)-1,2-aziridinedicarboxylate(104597-98-0) Related Product Information
1-Benzyl 2-methyl (S)-(-)-1,2-aziridinedicarboxylate Aziridine-2-carboxylic acid methyl ester Aziridine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (S)-2-Aziridinecarboxylic Acid Methyl Ester (R)-1-benzyloxycarbonyl-2-methoxycarbonylaziridine Methyl 1-(triphenylmethyl)-2-aziridinecarboxylate