N-Cbz-D-Asparagine

Name: N-Cbz-D-Asparagine
Brand: ChemScene
Availability: InStock
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CAS No. 4474-86-6
Cat. No. CS-0149990
Purity≥98%
MDL No.MFCD00065696

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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General Information

CAS No. 4474-86-6
Cat. No. CS-0149990
Purity ≥98%
MDL No. MFCD00065696
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₄N₂O₅
Molecular Weight 266.25
Synonym(s) Z-D-Asn-OH
SMILES NC(C[C@H](C(O)=O)NC(OCC1=CC=CC=C1)=O)=O

Description

N-Cbz-D-Asparagine features a D-configured asparagine residue protected at the α-amino group with a carbobenzoxy (Cbz) moiety. This configuration enables selective incorporation into peptide sequences requiring D-amino acid placement, while the Cbz group offers stable protection under standard coupling conditions and facilitates efficient deprotection via hydrogenolysis.

Application

N-Cbz-D-Asparagine serves as a key chiral building block for the synthesis of D-aspartate-containing peptides and heterocyclic scaffolds. The Cbz group provides robust protection of the amine, enabling orthogonal handling with other functional groups. It exhibits excellent bench stability and facilitates efficient coupling reactions under standard peptide synthesis conditions. Its defined stereochemistry and compatibility with common deprotection protocols make it a reliable choice for medicinal chemistry and API intermediate development.

Synthesis

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References
- E. R. Squibb and Sons, Inc. Patent: US642 H1, 1989 ;
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References
- Okamoto, Yoshio; Aburatani, Ryo; Kaida, Yuriko; Hatada, Koichi Chemistry Letters, 1988 , p. 1125 - 1128
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  2058-58-4
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References
- Zhang, Zhenyu; Aerschot, Arthur Van; Hendrix, Chris; Busson, Roger; David, Frank; Sandra, Pat; Herdewijn, Piet Tetrahedron, 2000 , vol. 56, # 16 p. 2513 - 2522

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 118.72
LogP 0.2414
H_Acceptors 4
H_Donors 3
Rotatable_Bonds 6

Other Classifications

Building Blocks Functional Group Amide

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

Chemical Biology Pharmaceutical Development and Drug Discovery Research Reagents Peptide Chemistry Amino Acid Derivatives

Chemical Biology Pharmaceutical Development and Drug Discovery Research Peptide Chemistry Amino Acid Derivatives

Biochemistry Biochemicals and Reagents Amino Acids N-Protected Amino Acids

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N-Cbz-D-Asparagine

CAS No. 4474-86-6

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