(S)-Ethyl 4-amino-2-((tert-butoxycarbonyl)amino)-4-oxobutanoate

Name: (S)-Ethyl 4-amino-2-((tert-butoxycarbonyl)amino)-4-oxobutanoate
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CAS No. 84787-81-5
Cat. No. CS-0151939
Purity≥96%
MDL No.MFCD15141969

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(S)-Ethyl 4-amino-2-((tert-butoxycarbonyl)amino)-4-oxobutanoate|CS-0151939

Structure of 84787-81-5

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General Information

CAS No. 84787-81-5
Cat. No. CS-0151939
Purity ≥96%
MDL No. MFCD15141969
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₂₀N₂O₅
Molecular Weight 260.29
Synonym(s) N2-[(1,1-Dimethylethoxy)carbonyl]-L-asparagine ethyl ester
SMILES CCOC([C@@H](NC(OC(C)(C)C)=O)CC(N)=O)=O

Description

(S)-Ethyl 4-amino-2-((tert-butoxycarbonyl)amino)-4-oxobutanoate features a chiral center and a protected α-amino carbonyl motif, enabling direct incorporation into peptide backbones. The tert-butyl carbamate group ensures stability during synthetic manipulations, while the ethyl ester facilitates selective derivatization. This building block supports efficient access to non-proteinogenic amino acid scaffolds under standard conditions.

Application

(S)-Ethyl 4-amino-2-((tert-butoxycarbonyl)amino)-4-oxobutanoate serves as a key chiral building block for the synthesis of β-lactam antibiotics and peptidomimetics. Its protected amine and ester functionalities enable orthogonal transformations, while the α-amino ketone moiety facilitates stereoselective cyclizations. The tert-butyl carbamate group provides stability and ease of removal under mild acidic conditions, enhancing its utility in multi-step synthetic sequences.

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 107.72
LogP 0.3182
H_Acceptors 5
H_Donors 2
Rotatable_Bonds 5

Other Classifications

Building Blocks Functional Group Ester

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Life Science Amino Acids and their Derivatives Asparagine and derivatives

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

Key Words

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(S)-Ethyl 4-amino-2-((tert-butoxycarbonyl)amino)-4-oxobutanoate

CAS No. 84787-81-5

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