(R)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4,4-difluoropyrrolidine-2-carboxylic acid

Name: (R)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4,4-difluoropyrrolidine-2-carboxylic acid
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CAS No. 273222-07-4
Cat. No. CS-0626856
Purity≥95%
MDL No.MFCD01860710

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(R)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4,4-difluoropyrrolidine-2-carboxylic acid|CS-0626856

Structure of 273222-07-4

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Description

(R)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4,4-difluoropyrrolidine-2-carboxylic acid is a chiral building block featuring a sterically constrained pyrrolidine core with a fluorenylmethyl carbamate protecting group. This configuration enables reliable incorporation into peptide sequences under standard coupling conditions. The 4,4-difluoro substitution enhances metabolic stability and modulates conformational flexibility. The fluorenylmethyl moiety facilitates efficient purification via crystallization or chromatography.

Application

(R)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4,4-difluoropyrrolidine-2-carboxylic acid serves as a valuable chiral building block in peptide synthesis, leveraging the robustness of Fmoc protection. The 4,4-difluoropyrrolidine moiety imparts enhanced metabolic stability and conformational rigidity, facilitating structural modulation in bioactive peptides. Its bench-stable nature and compatibility with standard coupling protocols enable efficient incorporation into complex scaffolds.

General Information

CAS No. 273222-07-4
Cat. No. CS-0626856
Purity ≥95%
MDL No. MFCD01860710
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₀H₁₇F₂NO₄
Molecular Weight 373.35
Synonym(s) None
SMILES O=C(N1[C@H](CC(F)(C1)F)C(O)=O)OCC2C3=CC=CC=C3C4=CC=CC=C42

Computational Chemistry Data

TPSA 66.84
LogP 3.7297
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 3

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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Other Classifications

Building Blocks Functional Group Fluoride

Building Blocks Functional Group Carboxylic Acid

Building Blocks Functional Group Ester

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrrolidine compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Key Words

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(R)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4,4-difluoropyrrolidine-2-carboxylic acid

CAS No. 273222-07-4

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