Fmoc-(2S,4S)-4-phenyl-pyrrolidine-2-carboxylic acid

Name: Fmoc-(2S,4S)-4-phenyl-pyrrolidine-2-carboxylic acid
Brand: ChemScene
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CAS No. 269078-71-9
Cat. No. CS-0060483
Purity≥98%
MDL No.None

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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+
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Fmoc-(2S,4S)-4-phenyl-pyrrolidine-2-carboxylic acid|CS-0060483

Structure of 269078-71-9

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General Information

CAS No. 269078-71-9
Cat. No. CS-0060483
Purity ≥98%
MDL No. None
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₆H₂₃NO₄
Molecular Weight 413.47
Synonym(s) (2S,4S)-FMOC-4-PHENYL-PYRROLIDINE-2-CARBOXYLIC ACID
SMILES C1=CC=C(C=C1)[C@@H]2C[C@@H](C(=O)O)N(C2)C(=O)OCC3C4=CC=CC=C4C5=CC=CC=C53

Description

Fmoc-(2S,4S)-4-phenyl-pyrrolidine-2-carboxylic acid is a stereochemically defined building block for peptide synthesis, featuring a rigid pyrrolidine core with a phenyl-substituted C4 position. The Fmoc group enables efficient N-terminal protection, while the chiral 2S,4S configuration supports precise conformational control in folded peptide architectures. This derivative combines synthetic robustness with structural predictability, streamlining access to bioactive peptidomimetics.

Application

Fmoc-(2S,4S)-4-phenyl-pyrrolidine-2-carboxylic acid serves as a valuable chiral building block for the synthesis of peptidomimetics and bioactive heterocycles. The Fmoc group enables efficient solid-phase peptide synthesis, while the (2S,4S)-configured pyrrolidine core provides defined stereochemistry and conformational rigidity. Its phenyl-substituted ring enhances π-stacking potential and metabolic stability, facilitating incorporation into diverse scaffolds with predictable reactivity in standard coupling protocols.

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-P330-P362+P364-P405-P501

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Computational Chemistry Data

TPSA 66.84
LogP 4.8782
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 4

Other Classifications

Building Blocks Functional Group Carboxylic Acid

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrrolidine compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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Fmoc-(2S,4S)-4-phenyl-pyrrolidine-2-carboxylic acid

CAS No. 269078-71-9

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