(R)-2-Amino-4-methoxy-4-oxobutanoic acid

Name: (R)-2-Amino-4-methoxy-4-oxobutanoic acid
Brand: ChemScene
Availability: InStock
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CAS No. 21394-81-0
Cat. No. CS-0059140
Molecule weight147.13
Purity≥97%
MDL No.None

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Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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(R)-2-Amino-4-methoxy-4-oxobutanoic acid|CS-0059140

Structure of 21394-81-0

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General Information

CAS No. 21394-81-0
Cat. No. CS-0059140
Purity ≥97%
MDL No. None
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₅H₉NO₄
Molecular Weight 147.13
Synonym(s) H-D-Asp(OMe)-OH·HCl
SMILES N[C@H](CC(OC)=O)C(O)=O

Description

(R)-2-Amino-4-methoxy-4-oxobutanoic acid features a stereochemically defined chiral center critical for asymmetric synthesis. The molecule integrates a carboxylic acid, amine, and methoxy-substituted ketone within a linear four-carbon framework, enabling direct incorporation into peptide mimetics and bioactive heterocycles under standard conditions. This bench-stable derivative supports efficient derivatization in medicinal chemistry workflows.

Application

(R)-2-Amino-4-methoxy-4-oxobutanoic acid serves as a key chiral building block for synthesizing bioactive heterocycles and peptidomimetics. Its well-defined stereochemistry enables reliable incorporation into complex scaffolds, while the α-amino and β-ketoester functionalities offer orthogonal reactivity for sequential transformations. Bench-stable and amenable to standard purification methods, it facilitates efficient access to medicinally relevant frameworks in both academic and industrial settings.

Synthesis

Route1
- 6384-18-5
- ~92%
- In-stock
  
  21394-81-0
References
- Stein, Karin A.; Toogood, Peter L. Journal of Organic Chemistry, 1995 , vol. 60, # 24 p. 8110 - 8112
Route2
- 67-56-1
- In-stock
  
  1783-96-6
- ~%
- In-stock
  
  21394-81-0
References
- Gazzetta Chimica Italiana, , vol. 116, # 10 p. 607 - 608
Route3
- In-stock
  
  2177-62-0
- ~%
- In-stock
  
  21394-81-0
References
- Journal of Organic Chemistry, , vol. 54, # 19 p. 4529 - 4535

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 89.62
LogP -1.0386
H_Acceptors 4
H_Donors 2
Rotatable_Bonds 3

Other Classifications

Life Science Amino Acids and their Derivatives Aspartic acid and derivatives

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

Key Words

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(R)-2-Amino-4-methoxy-4-oxobutanoic acid

CAS No. 21394-81-0

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