(r)-2-((Tert-butoxycarbonyl)amino)-3,3-dimethylpent-4-enoic acid

Name: (r)-2-((Tert-butoxycarbonyl)amino)-3,3-dimethylpent-4-enoic acid
Brand: ChemScene
Availability: InStock
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CAS No. 854250-89-8
Cat. No. CS-0673218
Purity≥98%
MDL No.MFCD18762149

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Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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(r)-2-((Tert-butoxycarbonyl)amino)-3,3-dimethylpent-4-enoic acid|CS-0673218

Structure of 854250-89-8

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General Information

CAS No. 854250-89-8
Cat. No. CS-0673218
Purity ≥98%
MDL No. MFCD18762149
Storage 4°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₂₁NO₄
Molecular Weight 243.30
Synonym(s) None
SMILES CC(C)(C)OC(=O)N[C@@H](C(=O)O)C(C)(C)C=C

Description

(r)-2-((Tert-butoxycarbonyl)amino)-3,3-dimethylpent-4-enoic acid features a sterically hindered, bench-stable α,β-unsaturated carbonyl system paired with a protected amine. This configuration enables direct incorporation into peptide synthesis workflows and facilitates downstream deprotection under mild acidic conditions. The molecule’s conjugated enoate moiety supports efficient coupling reactions while maintaining stability during storage and handling.

Application

(r)-2-((Tert-butoxycarbonyl)amino)-3,3-dimethylpent-4-enoic acid serves as a versatile chiral building block for the synthesis of peptidomimetics and bioactive heterocycles. The protected amine and terminal alkyne functionalities enable efficient coupling reactions and downstream transformations, including palladium-catalyzed cross-couplings and cyclizations. Its tert-butyl carbamate group provides excellent stability and ease of purification, while the (r)-configuration ensures stereochemical fidelity in complex molecule assembly.

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

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Computational Chemistry Data

TPSA 75.63
LogP 2.1765
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 4

Other Classifications

Building Blocks Functional Group Olefins

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Fatty chain compounds

Life Science Amino Acids and their Derivatives Valine and derivatives

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

Key Words

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(r)-2-((Tert-butoxycarbonyl)amino)-3,3-dimethylpent-4-enoic acid

CAS No. 854250-89-8

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