516031

Methyl-(S)-(−)-N-Z-aziridin-2-carboxylat

96%

• Synonym(e): (2S)-1,2-Aziridinedicarboxylic acid 2-methyl 1-(phenylmethyl) ester, (S)-N-Cbz-aziridine-2-carboxylic acid methyl ester, 1-Benzyl 2-methyl (S)-(−)-1,2-aziridinedicarboxylate, Methyl (S)-N-Cbz-aziridine-2-carboxylate
• Empirische Formel (Hill-System): C₁₂H₁₃NO₄
• CAS-Nummer: 104597-98-0
• Molekulargewicht: 235.24
• MDL-Nummer: MFCD06799020
• UNSPSC-Code: 12352005
• PubChem Substanz-ID: 24873860
• NACRES: NA.22

Eigenschaften

• Assay: 96%
• Optische Aktivität: [α]20/D −25°, c = 1 in toluene
• Brechungsindex: n20/D 1.519 (lit.)
• bp: 160-165 °C/2 mmHg (lit.)
• Dichte: 1.19 g/mL at 25 °C (lit.)
• SMILES String: COC(=O)C1CN1C(=O)OCc2ccccc2
• InChI: 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
• InChIKey: GTZJUBQWCWZING-NKUHCKNESA-N

Beschreibung

Allgemeine Beschreibung

Methyl (S)-(−)-N-Z-aziridine-2-carboxylate is commonly used as an electrophilic aziridination reagent in organic synthesis. It is a chiral bicyclic lactam reagent that can be used for the synthesis of chiral aziridines from alkenes. The reagent is particularly useful in the synthesis of chiral building blocks.

Anwendung

Methyl (S)-(−)-N-Z-aziridine-2-carboxylate can be used as a reactant in the total synthesis of α-C-mannosyltryptophan (C-Man-Trp), a naturally occurring C-glycosylamino acid. It is also used in the preparation of optically active aziridine derivatives.

Sicherheitshinweise

• Lagerklassenschlüssel: 10 - Combustible liquids
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable
• Persönliche Schutzausrüstung: Eyeshields, Gloves