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227781 Sigma-Aldrich

N-(Benzyloxycarbonyloxy)succinimide

98%

Synonym: Benzyl N-succinimidyl carbonate, Z-OSu

  • CAS Number 13139-17-8

  • Empirical Formula (Hill Notation) C12H11NO5

  • Molecular Weight 249.22

  •  Beilstein/REAXYS Number 1387927

  •  EC Number 236-075-3

  •  MDL number MFCD00005513

  •  PubChem Substance ID 24853653

  •  NACRES NA.22

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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.

Packaging

25, 100, 250 g in poly bottle

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
3

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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