(R)-4-(tert-Butoxy)-2-((tert-butoxycarbonyl)amino)-4-oxobutanoic acid

Name: (R)-4-(tert-Butoxy)-2-((tert-butoxycarbonyl)amino)-4-oxobutanoic acid
Brand: ChemScene
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CAS No. 155542-33-9
Cat. No. CS-0135753
Purity≥95%
MDL No.MFCD01861313

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Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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(R)-4-(tert-Butoxy)-2-((tert-butoxycarbonyl)amino)-4-oxobutanoic acid|CS-0135753

Structure of 155542-33-9

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General Information

CAS No. 155542-33-9
Cat. No. CS-0135753
Purity ≥95%
MDL No. MFCD01861313
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₂₃NO₆
Molecular Weight 289.32
Synonym(s) D-Aspartic acid, N-[(1,1-diMethylethoxy)carbonyl]-, 4-(1,1-diMethylethyl) ester
SMILES O=C(OC(C)(C)C)C[C@H](C(O)=O)NC(OC(C)(C)C)=O

Description

(R)-4-(tert-Butoxy)-2-((tert-butoxycarbonyl)amino)-4-oxobutanoic acid features a stereodefined chiral center and combines a protected amine with a ketone and ester functionality. This multifunctional building block enables direct incorporation into complex molecular architectures under standard conditions, supporting efficient synthesis of bioactive compounds.

Application

(R)-4-(tert-Butoxy)-2-((tert-butoxycarbonyl)amino)-4-oxobutanoic acid serves as a key chiral building block for synthesizing bioactive β-amino acid derivatives and peptidomimetics. The molecule combines a stable tert-butyl ester, a robust Boc-protected amine, and a ketone-functionalized chain, enabling sequential transformations under standard peptide coupling and reductive amination conditions. Its bench-stable nature and orthogonal functional group tolerance facilitate efficient access to complex heterocyclic scaffolds and drug-like intermediates in medicinal chemistry campaigns.

Synthesis

Route1
- In-stock
  
  24424-99-5
- In-stock
  
  64960-75-4
- ~10%
- In-stock
  
  155542-33-9
References
- Henry, Luc; Leung, Ivanhoe K.H.; Claridge, Timothy D.W.; Schofield, Christopher J. Bioorganic and Medicinal Chemistry Letters, 2012 , vol. 22, # 15 p. 4975 - 4978

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 101.93
LogP 1.6961
H_Acceptors 5
H_Donors 2
Rotatable_Bonds 4

Other Classifications

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

Key Words

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(R)-4-(tert-Butoxy)-2-((tert-butoxycarbonyl)amino)-4-oxobutanoic acid

CAS No. 155542-33-9

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