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227781

Sigma-Aldrich

N-(Benzyloxycarbonyloxy)succinimide

98%, for peptide synthesis

Synonym(s):

Benzyl N-succinimidyl carbonate, Z-OSu

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About This Item

Empirical Formula (Hill Notation):
C12H11NO5
CAS Number:
Molecular Weight:
249.22
Beilstein/REAXYS Number:
1387927
EC Number:
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

product name

N-(Benzyloxycarbonyloxy)succinimide, 98%

Quality Level

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

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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.

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)


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Reconstitution of peptidoglycan cross-linking leads to improved fluorescent probes of cell wall synthesis.
Lebar M D, et al.
Journal of the American Chemical Society, 136(31), 10874-10877 (2014)
Total synthesis of nominal Diazonamides?Part 1: convergent preparation of the structure proposed for (−)?Diazonamide A.
Li J, et al.
Angewandte Chemie (International Edition in English), 40(24), 4765-4769 (2001)
A convergent three-component total synthesis of the powerful immunosuppressant (−)-sanglifehrin A.
Paquette L A, et al.
Journal of the American Chemical Society, 124(16), 4257-4270 (2002)
Pd/C (en)-Catalyzed chemoselective hydrogenation with retention of the N-Cbz protective group and its scope and limitations.
Hattori K, et al.
Tetrahedron, 56(43), 8433-8441 (2000)
A general asymmetric synthesis of syn-and anti-β-substituted cysteine and serine derivatives.
Xiong C, et al.
The Journal of Organic Chemistry, 67(10), 3514-3517 (2002)

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