(2S,4S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

Name: (2S,4S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acid
Brand: ChemScene
Availability: InStock
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CAS No. 189249-10-3
Cat. No. CS-W021075
Purity≥97%
MDL No.MFCD02682328

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(2S,4S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acid|CS-W021075

Structure of 189249-10-3

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General Information

CAS No. 189249-10-3
Cat. No. CS-W021075
Purity ≥97%
MDL No. MFCD02682328
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₀H₁₉NO₅
Molecular Weight 353.37
Synonym(s) Fmoc-(2S,4S)-(-)-4-hydroxypyrrolidine-2-carboxylic acid
SMILES O=C([C@H]1N(C(OCC2C3=C(C4=C2C=CC=C4)C=CC=C3)=O)C[C@@H](O)C1)O

Description

This fluorenylmethoxycarbonyl-protected pyrrolidine derivative features a chiral (2S,4S) core with a hydroxyl group at C4 and a carboxylic acid at C2, enabling direct incorporation into peptide synthesis workflows. The Fmoc moiety provides orthogonal protection, while the stereochemistry ensures high diastereoselectivity in coupling reactions. Designed for efficient solid-phase and solution-phase assembly of complex peptidomimetics and cyclic peptides.

Application

(2S,4S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acid serves as a chiral building block for peptide synthesis and medicinal chemistry applications. The Fmoc group enables orthogonal protection in solid-phase peptide synthesis, while the C4 hydroxyl group provides a site for derivatization or stereocontrolled transformations. Its bench-stable nature and compatibility with standard coupling conditions facilitate efficient incorporation into complex molecular architectures.

Synthesis

Route1
- 28920-43-6
- In-stock
  
  618-27-9
- ~92%
- In-stock
  
  189249-10-3
References
- Taylor, Carol M.; Hardre, Renaud; Edwards, Patrick J. B. Journal of Organic Chemistry, 2005 , vol. 70, # 4 p. 1306 - 1315

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

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Computational Chemistry Data

TPSA 87.07
LogP 2.4553
H_Acceptors 4
H_Donors 2
Rotatable_Bonds 3

Other Classifications

Building Blocks Functional Group Fmoc

Building Blocks Functional Group Alcohol

Building Blocks Functional Group Carboxylic Acid

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrrolidine compounds

Chemical Biology Peptide Chemistry Amino Acid Derivatives

Key Words

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(2S,4S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

CAS No. 189249-10-3

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