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Merck

227781

Sigma-Aldrich

N-(Benzyloxycarbonyloxy)succinimide

98%, for peptide synthesis

Sinónimos:

Benzyl N-succinimidyl carbonate, Z-OSu

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About This Item

Fórmula empírica (notación de Hill):
C12H11NO5
Número de CAS:
Peso molecular:
249.22
Beilstein:
1387927
Número CE:
Número MDL:
Código UNSPSC:
12352005
ID de la sustancia en PubChem:
NACRES:
NA.22
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Nombre del producto

N-(Benzyloxycarbonyloxy)succinimide, 98%

Nivel de calidad

Ensayo

98%

mp

80-82 °C (lit.)

aplicaciones

peptide synthesis

grupo funcional

imide
phenyl

cadena SMILES

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

Clave InChI

MJSHDCCLFGOEIK-UHFFFAOYSA-N

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Aplicación

N-(Benzyloxycarbonyloxy)succinimide (Cbz-OSu) is a common reagent for the carboxybenzyl protection of amines.[1] 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.[2]
  • 1′-H-Spiro-(indoline-3,4′-piperidine) and its derivatives.[3]
  • Total synthesis of (-)-diazonamide A.[4] and (-)-sanglifehrin A.[5]

Cbz-OSu is widely employed to protect amino acid residues in peptide synthesis.[6][7] It can also be used in N-trans diprotection of cyclen regioselectively.[8]
Reagent for the selective introduction of the Z-amino protection in amino acids; and in aminoglycoside antibiotics.

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)


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Los clientes también vieron

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 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)
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)
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)

Questions

1–2 of 2 Questions  
  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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