(R)-2-(((Benzyloxy)carbonyl)amino)pent-4-enoic acid

Name: (R)-2-(((Benzyloxy)carbonyl)amino)pent-4-enoic acid
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CAS No. 127474-54-8
Cat. No. CS-0059999
Molecule weight249.26
Purity≥97%
MDL No.None

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(R)-2-(((Benzyloxy)carbonyl)amino)pent-4-enoic acid|CS-0059999

Structure of 127474-54-8

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General Information

CAS No. 127474-54-8
Cat. No. CS-0059999
Purity ≥97%
MDL No. None
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₁₅NO₄
Molecular Weight 249.26
Synonym(s) CBZ-ALPHA-ALLYL-D-GLY
SMILES C=CC[C@@H](NC(OCC1=CC=CC=C1)=O)C(O)=O

Description

(R)-2-(((Benzyloxy)carbonyl)amino)pent-4-enoic acid is a chiral, unsaturated amino acid derivative featuring a conjugated double bond and a labile benzyloxycarbonyl protecting group. This structure enables selective coupling in peptide synthesis workflows, where the Cbz moiety facilitates orthogonal deprotection under mild hydrogenolysis conditions. The molecule's stability under standard bench handling supports reliable integration into complex synthetic sequences.

Application

(R)-2-(((Benzyloxy)carbonyl)amino)pent-4-enoic acid serves as a valuable chiral building block for the synthesis of peptidomimetics and bioactive heterocycles. The protected α-amino acid functionality enables straightforward incorporation into peptide sequences, while the terminal alkene supports downstream transformations such as metathesis or conjugate addition. Bench-stable and amenable to standard purification methods, it facilitates efficient access to complex scaffolds in medicinal chemistry campaigns.

Safety Information

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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

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Computational Chemistry Data

TPSA 75.63
LogP 1.9421
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 6

Other Classifications

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Life Science Amino Acids and their Derivatives Alanine and derivatives

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

Key Words

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(R)-2-(((Benzyloxy)carbonyl)amino)pent-4-enoic acid

CAS No. 127474-54-8

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