(2S,3R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylbutanoic acid

Name: (2S,3R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylbutanoic acid
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CAS No. 321524-83-8
Cat. No. CS-0438328
Purity≥98%
MDL No.None

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(2S,3R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylbutanoic acid|CS-0438328

Structure of 321524-83-8

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General Information

CAS No. 321524-83-8
Cat. No. CS-0438328
Purity ≥98%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₅H₂₃NO₄
Molecular Weight 401.45
Synonym(s) L-Phenylalanine,N-((9H-fluoren-9-ylmethoxy)carbonyl)-β-meth
SMILES C[C@H](C1=CC=CC=C1)[C@@H](C(O)=O)NC(OCC2C3=CC=CC=C3C4=CC=CC=C42)=O

Description

(2S,3R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylbutanoic acid serves as a chiral building block for peptide synthesis, featuring a fluorenylmethyl carbamate (Fmoc) protecting group and a sterically defined side chain. This configuration enables efficient coupling under standard conditions, with the phenylbutanoyl moiety providing structural rigidity and enhanced solubility in organic media.

Application

(2S,3R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylbutanoic acid serves as a well-established chiral building block for peptide synthesis, offering high stereochemical fidelity and compatibility with standard coupling protocols. The Fmoc group enables convenient N-terminal protection with orthogonal deprotection under mild basic conditions. Its phenyl-substituted aliphatic side chain provides structural rigidity and enhances metabolic stability, making it suitable for the synthesis of bioactive peptides and peptidomimetics requiring defined stereochemistry and improved solubility.

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 : H315-H319-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362-P501

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Computational Chemistry Data

TPSA 75.63
LogP 4.782
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 6

Other Classifications

Building Blocks Functional Group Fmoc

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

Key Words

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(2S,3R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylbutanoic acid

CAS No. 321524-83-8

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