(R)-3-((tert-Butoxycarbonyl)amino)-3-(naphthalen-2-yl)propanoic acid

Name: (R)-3-((tert-Butoxycarbonyl)amino)-3-(naphthalen-2-yl)propanoic acid
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CAS No. 500789-01-5
Cat. No. CS-0046078
Molecule weight315.36
Purity≥98%
MDL No.MFCD03427953

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(R)-3-((tert-Butoxycarbonyl)amino)-3-(naphthalen-2-yl)propanoic acid|CS-0046078

Structure of 500789-01-5

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General Information

CAS No. 500789-01-5
Cat. No. CS-0046078
Purity ≥98%
MDL No. MFCD03427953
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₈H₂₁NO₄
Molecular Weight 315.36
Synonym(s) (R)-Boc-3-(2-naphthyl)-beta-Ala-OH
SMILES O=C(O)[C@H](NC(OC(C)(C)C)=O)CC1=CC=C2C=CC=CC2=C1

Description

(R)-3-((tert-Butoxycarbonyl)amino)-3-(naphthalen-2-yl)propanoic acid is a chiral building block featuring a sterically hindered tert-butoxycarbonyl-protected amine and a naphthalene moiety. This configuration enables direct incorporation into peptide synthesis workflows, where the protected amine facilitates selective coupling under standard conditions. The rigid aromatic system enhances structural definition in final products, improving stereochemical fidelity during downstream transformations.

Application

(R)-3-((tert-Butoxycarbonyl)amino)-3-(naphthalen-2-yl)propanoic acid serves as a key chiral building block for the synthesis of biologically relevant β-amino acid derivatives. The protected amine and carboxylic acid functionalities enable orthogonal transformations, while the naphthalene moiety provides a rigid aromatic scaffold useful in medicinal chemistry. Bench-stable and compatible with standard peptide coupling protocols, it facilitates efficient access to peptidomimetics and heterocyclic scaffolds via cyclization or further functionalization.

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

Quality Control

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Computational Chemistry Data

TPSA 75.63
LogP 3.3602
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 4

Other Classifications

Life Science Amino Acids and their Derivatives Alanine and derivatives

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

Key Words

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(R)-3-((tert-Butoxycarbonyl)amino)-3-(naphthalen-2-yl)propanoic acid

CAS No. 500789-01-5

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