(2s,4s)-1-(((9h-Fluoren-9-yl)methoxy)carbonyl)-4-(trifluoromethyl)pyrrolidine-2-carboxylic acid

Name: (2s,4s)-1-(((9h-Fluoren-9-yl)methoxy)carbonyl)-4-(trifluoromethyl)pyrrolidine-2-carboxylic acid
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CAS No. 1242934-32-2
Cat. No. CS-0216097
Molecule weight405.37
Purity≥96%
MDL No.None

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(2s,4s)-1-(((9h-Fluoren-9-yl)methoxy)carbonyl)-4-(trifluoromethyl)pyrrolidine-2-carboxylic acid|CS-0216097

Structure of 1242934-32-2

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General Information

CAS No. 1242934-32-2
Cat. No. CS-0216097
Purity ≥96%
MDL No. None
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₁H₁₈F₃NO₄
Molecular Weight 405.37
Synonym(s) (2S,4S)-Fmoc-4-trifluoromethyl-pyrrolidine-2-carboxylic acid
SMILES O=C([C@H]1N(C(OCC2C3=C(C4=C2C=CC=C4)C=CC=C3)=O)C[C@@H](C(F)(F)F)C1)O

Description

This fluoren-9-ylmethoxycarbonyl-protected pyrrolidine derivative features a sterically hindered, electron-deficient trifluoromethyl group at the C4 position, enabling efficient incorporation into peptide synthesis. The robust Fmoc moiety ensures stable anchoring during chain elongation and facilitates straightforward deprotection under mild basic conditions.

Application

(2S,4S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4-(trifluoromethyl)pyrrolidine-2-carboxylic acid serves as a versatile chiral building block for the synthesis of peptidomimetics and bioactive heterocycles. The Cbz-protected pyrrolidine scaffold exhibits excellent bench stability, facilitates efficient purification, and tolerates diverse functional groups. It enables robust coupling reactions and functions effectively in solid-phase peptide synthesis and catalytic asymmetric transformations.

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-P405-P501

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Computational Chemistry Data

TPSA 66.84
LogP 4.2729
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 3

Other Classifications

Building Blocks Functional Group Fluoride

Building Blocks Functional Group Carboxylic Acid

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrrolidine compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Key Words

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(2s,4s)-1-(((9h-Fluoren-9-yl)methoxy)carbonyl)-4-(trifluoromethyl)pyrrolidine-2-carboxylic acid

CAS No. 1242934-32-2

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