227781

N-(Benzyloxycarbonyloxy)succinimide

98%

• Synonym(s): Benzyl N-succinimidyl carbonate, Z-OSu
• Empirical Formula (Hill Notation): C₁₂H₁₁NO₅
• CAS Number: 13139-17-8
• Molecular Weight: 249.22
• Beilstein/REAXYS Number: 1387927
• EC Number: 236-075-3
• MDL number: MFCD00005513
• UNSPSC Code: 12352005
• PubChem Substance ID: 24853653
• NACRES: NA.22

Properties

• Quality Level: 200
• assay: 98%
• mp: 80-82 °C (lit.)
• application(s): peptide synthesis
• SMILES string: 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
• InChI key: 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.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)