N-Boc-3-(4-biphenylyl)-D-alanine

Name: N-Boc-3-(4-biphenylyl)-D-alanine
Brand: ChemScene
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CAS No. 128779-47-5
Cat. No. CS-W023100
Purity≥98%
MDL No.MFCD00191185

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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N-Boc-3-(4-biphenylyl)-D-alanine|CS-W023100

Structure of 128779-47-5

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General Information

CAS No. 128779-47-5
Cat. No. CS-W023100
Purity ≥98%
MDL No. MFCD00191185
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₀H₂₃NO₄
Molecular Weight 341.41
Synonym(s) Boc-D-4-Phenylphenylalanine
SMILES OC([C@@H](CC(C=C1)=CC=C1C2=CC=CC=C2)N(C(OC(C)(C)C)=O)[H])=O

Description

N-Boc-3-(4-biphenylyl)-D-alanine features a D-alanine backbone functionalized with a bulky, electron-rich biphenyl group at the C3 position and a sterically shielded Boc protecting group. This configuration enhances stability during synthetic manipulations while enabling direct incorporation into peptide architectures requiring non-natural D-amino acid residues. The biphenyl moiety imparts conformational rigidity and improved membrane permeability, making it suitable for bioactive peptide synthesis.

Application

N-Boc-3-(4-biphenylyl)-D-alanine serves as a valuable chiral building block for the synthesis of D-amino acid-containing peptides and heterocyclic scaffolds. The Boc group provides excellent stability and ease of removal under mild acidic conditions, while the 4-biphenylyl side chain offers defined aromatic character and compatibility with standard coupling protocols. This derivative enables efficient access to biologically relevant motifs in medicinal chemistry campaigns requiring D-amino acid incorporation.

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 75.63
LogP 3.874
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 5

Other Classifications

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

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N-Boc-3-(4-biphenylyl)-D-alanine

CAS No. 128779-47-5

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