(R)-3-((tert-Butoxycarbonyl)amino)-4-phenylbutanoic acid

Name: (R)-3-((tert-Butoxycarbonyl)amino)-4-phenylbutanoic acid
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CAS No. 101555-61-7
Cat. No. CS-0036367
Purity≥97%
MDL No.MFCD01076270

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(R)-3-((tert-Butoxycarbonyl)amino)-4-phenylbutanoic acid|CS-0036367

Structure of 101555-61-7

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General Information

CAS No. 101555-61-7
Cat. No. CS-0036367
Purity ≥97%
MDL No. MFCD01076270
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₅H₂₁NO₄
Molecular Weight 279.33
Synonym(s) Boc-d-beta-homophenylalanine
SMILES O=C(O)C[C@H](NC(OC(C)(C)C)=O)CC1=CC=CC=C1

Description

(R)-3-((tert-Butoxycarbonyl)amino)-4-phenylbutanoic acid is a chiral building block featuring a protected amino group and a phenyl-substituted aliphatic chain. This bench-stable derivative enables efficient incorporation into peptide sequences and serves as a key intermediate in the synthesis of bioactive compounds, particularly those requiring stereocontrolled side-chain functionality.

Application

(R)-3-((tert-Butoxycarbonyl)amino)-4-phenylbutanoic acid serves as a versatile chiral building block for the synthesis of bioactive molecules, particularly in peptidomimetic and pharmaceutical scaffolds. The protected amine and carboxylic acid functionalities enable sequential coupling reactions with high fidelity, while the tert-butoxycarbonyl group offers excellent bench stability and orthogonal deprotection under mild acidic conditions. Its phenyl-substituted aliphatic chain provides structural rigidity and hydrophobic character useful in drug design.

Synthesis

Route1
- In-stock
  
  24424-99-5
- In-stock
  
  131270-08-1
- ~%
- In-stock
  
  101555-61-7
References
- WO2013/64231 A1, ; Page/Page column 55 ; WO 2013/064231 A1
Route2
- 115313-19-4
- ~90%
- In-stock
  
  101555-61-7
References
- Hernandez; Soleilhac; Roques; Fournie-Zaluski Journal of Medicinal Chemistry, 1988 , vol. 31, # 9 p. 1825 - 1831
Route3
- 177839-89-3
- ~87%
- In-stock
  
  101555-61-7
References
- Seki, Masahiko; Matsumoto, Kazuo Tetrahedron Letters, 1996 , vol. 37, # 18 p. 3165 - 3168

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 75.63
LogP 2.5971
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 5

Other Classifications

Building Blocks Functional Group Carboxylic Acid

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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(R)-3-((tert-Butoxycarbonyl)amino)-4-phenylbutanoic acid

CAS No. 101555-61-7

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