N-(Benzyloxycarbonyloxy)succinimide

Description

Benzyl N-succinimidyl carbonate (Cbz-OSu) is usually used for the Cbz protection of amines. A similar reagent is benzyl chloroformate.

Chemical properties

white crystal powde

The Uses of N-(Benzyloxycarbonyloxy)succinimide

Reagents for the selective introduction of the Z-protecting group into amino compounds

The Uses of N-(Benzyloxycarbonyloxy)succinimide

To a solution of the SM (30.5 g, 148.6 mmol) in THF/H2O (1:1, 400 mL) was added NaHCO3 (24.7 g, 294 mmol), followed by benzyl N-succinimidyl carbonate (44.0 g, 176 mmol) at RT. The reaction was stirred at RT for 4 h, after which time the layers were separated and the aq layer was further extracted with EtOAc (2x). The combined organics were washed with brine, dried (MgSO4), concentrated, and purified by silica gel chromatography (0-60% EtOAc/hexane) to provide the product as a yellow oil. [44.8 g, 89%]

The Uses of N-(Benzyloxycarbonyloxy)succinimide

N-(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.

The Uses of N-(Benzyloxycarbonyloxy)succinimide

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.