227781

N-(Benzyloxycarbonyloxy)succinimide

98%, for peptide synthesis

• Synonyme(s) : Benzyl N-succinimidyl carbonate, Z-OSu
• Formule empirique (notation de Hill): C₁₂H₁₁NO₅
• Numéro CAS: 13139-17-8
• Poids moléculaire : 249.22
• Numéro Beilstein : 1387927
• Numéro CE : 236-075-3
• Numéro MDL: MFCD00005513
• Code UNSPSC : 12352005
• ID de substance PubChem : 24853653
• Nomenclature NACRES : NA.22

Propriétés

• product name: N-(Benzyloxycarbonyloxy)succinimide, 98%
• Pureté: 98%
• Pf: 80-82 °C (lit.)
• Application(s): peptide synthesis
• Groupe fonctionnel: imide; phenyl
• Chaîne 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
• Clé InChI: MJSHDCCLFGOEIK-UHFFFAOYSA-N

Description

Application

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.

Informations sur la sécurité

• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable
• Équipement de protection individuelle: Eyeshields, Gloves, type N95 (US)