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N-(Benzyloxycarbonyloxy)succinimide

N-(Benzyloxycarbonyloxy)succinimide Basic information
Product Name:N-(Benzyloxycarbonyloxy)succinimide
Synonyms:BENZYLOXYCARBONYL-N-HYDROXYSUCCINIMIDE;BENZYLOXYLCARBONYLOXYSUCCINIMIDE;BENZYLOXYCARBONYLSUCCINIMIDE;BENZYLOXYCARBONYLOXYSUCCINIMIDE;BENZYL N-SUCCINIMIDYL CARBONATE;benzyl succinimido carbonate;CBZ-ONSU;CBZ-OSU
CAS:13139-17-8
MF:C12H11NO5
MW:249.22
EINECS:236-075-3
Product Categories:Medical Intermediates;Peptide coupling agents;Amino Acid Derivatives;Imidazoles, Pyrroles, Pyrazoles, Pyrrolidines;N-Protecting Reagents;Biochemistry;Condensation & Active Esterification;N-Substituted Maleimides, Succinimides & Phthalimides;N-Substituted Succinimides;Peptide Synthesis;Protective Reagents (Peptide Synthesis);Synthetic Organic Chemistry;Cbz-Amino acid series
Mol File:13139-17-8.mol
N-(Benzyloxycarbonyloxy)succinimide Structure
N-(Benzyloxycarbonyloxy)succinimide Chemical Properties
Melting point 80-82 °C(lit.)
Boiling point 392.32°C (rough estimate)
density 1.3189 (rough estimate)
refractive index 1.5560 (estimate)
Fp 81°C
storage temp. Keep in dark place,Inert atmosphere,2-8°C
solubility acetone: 0.1 g/mL, clear
form Fine Crystalline Powder
color White to off-white
Decomposition 81 ºC
Sensitive Moisture Sensitive
BRN 1387927
Stability:Stable. Moisture sensitive.
CAS DataBase Reference13139-17-8(CAS DataBase Reference)
Safety Information
Hazard Codes Xi,Xn
Risk Statements 43-24/25-36/37/38-20/21/22
Safety Statements 22-24/25-36-26
WGK Germany 3
F 8-10
HS Code 29252900
MSDS Information
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N-Benzyloxycarbonyloxy succinimide English
SigmaAldrich English
ACROS English
ALFA English
N-(Benzyloxycarbonyloxy)succinimide Usage And Synthesis
Chemical Propertieswhite crystal powde
UsesReagents for the selective introduction of the Z-protecting group into amino compounds
UsesN-(N-Benzyloxycarbonyloxy)succinimide is a reagent used in the preparation of peptide thioacids view peptide precursors. Also used in the preparation of amino glycoside derivatives for the function of topoisomerase for both human and bacterial inhibition.
UsesN-(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.
N-(Benzyloxycarbonyloxy)succinimide Preparation Products And Raw materials
Preparation Products1-(Benzyloxycarbonyl)-4-piperidinone-->BENZYL 3-PYRROLINE-1-CARBOXYLATE-->Cbz-D-Phenylalaninol-->N-Cbz-L-Leucine-->N-Cbz-D-Alanine-->DIBENZYL 2,2'-IMINOBIS(ETHYLCARBAMATE)-->BENZYL N-(3-HYDROXYPROPYL)CARBAMATE-->(S)-benzyl 3-(hydroxymethyl)piperazine-1-carboxylate-->(R)-PIPERIDINE-1,3-DICARBOXYLIC ACID 1-BENZYL ESTER-->N-CARBOBENZOXY-1,3-DIAMINOPROPANE HYDROCHLORIDE-->1-BENZYL 4-ETHYL PIPERIDINE-1,4-DICARBOXYLATE-->BENZYL 2-BROMOETHYLCARBAMATE-->N,N'-Bis(benzyloxycarbonyl)-L-cystine-->Benzyl 4-hydroxy-1-piperidinecarboxylate-->Cbz-L-tert-Leucine-->tert-Butyl 2-(1-(((Benzyloxy)carbonyl)amino)-2-methylpropan-2-yl)hydrazinecarboxylate
O-Phthalimide Benzyl isocyanate Benzyl chloride Calcium carbonate Bismaleimide Carbonate Benzyl alcohol H-hydroxy succinimide DIALIFOS METHOXYFENOZIDE Maleimide 9-Fluorenylmethyl chloroformate Benzyl chloroformate Benzyl Dimethyl carbonate Benzyl benzoate Benzyl nicotinate Sodium carbonate
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