227781

N-(Benzyloxycarbonyloxy)succinimide

98%, for peptide synthesis

• Sinónimos: Benzyl N-succinimidyl carbonate, Z-OSu
• Fórmula empírica (notación de Hill): C₁₂H₁₁NO₅
• Número de CAS: 13139-17-8
• Peso molecular: 249.22
• Beilstein: 1387927
• Número CE: 236-075-3
• Número MDL: MFCD00005513
• Código UNSPSC: 12352005
• ID de la sustancia en PubChem: 24853653
• NACRES: NA.22

Propiedades

• product name: N-(Benzyloxycarbonyloxy)succinimide, 98%
• Análisis: 98%
• mp: 80-82 °C (lit.)
• aplicaciones: peptide synthesis
• cadena SMILES: O=C(OCc1ccccc1)ON2C(=O)CCC2=O
• InChI: 1S/C12H11NO5/c14-10-6-7-11(15)13(10)18-12(16)17-8-9-4-2-1-3-5-9/h1-5H,6-8H2
• Clave InChI: MJSHDCCLFGOEIK-UHFFFAOYSA-N

Descripción

Aplicación

N-(Benzyloxycarbonyloxy)succinimide (Cbz-OSu) is a common reagent for the carboxybenzyl protection of amines. This reaction is one of the key synthetic steps in the synthesis of:

• Enantiomers of cyclic methionine analogs viz, (R)-and (S)-3-aminotetrahydrothiophene- 3-carboxylic acid.
• 1′-H-Spiro-(indoline-3,4′-piperidine) and its derivatives.
• Total synthesis of (-)-diazonamide A. and (-)-sanglifehrin A.

Cbz-OSu is widely employed to protect amino acid residues in peptide synthesis. It can also be used in N-trans diprotection of cyclen regioselectively.

Reagent for the selective introduction of the Z-amino protection in amino acids; and in aminoglycoside antibiotics.

Información de seguridad

• Código de clase de almacenamiento: 11 - Combustible Solids
• Clase de riesgo para el agua (WGK): WGK 3
• Punto de inflamabilidad (°F): Not applicable
• Punto de inflamabilidad (°C): Not applicable
• Equipo de protección personal: Eyeshields, Gloves, type N95 (US)