N-Boc-4,4-difluoro-L-proline methyl ester

Name: N-Boc-4,4-difluoro-L-proline methyl ester
Brand: ChemScene
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CAS No. 203866-17-5
Cat. No. CS-W001497
Purity≥98%
MDL No.MFCD03094918

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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+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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N-Boc-4,4-difluoro-L-proline methyl ester|CS-W001497

Structure of 203866-17-5

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Description

N-Boc-4,4-difluoro-L-proline methyl ester features a sterically constrained proline scaffold with dual fluorine atoms at the C4 position, enhancing conformational rigidity and metabolic stability. The Boc-protected amine and methyl ester functionality enable straightforward incorporation into peptide chains, facilitating efficient synthesis of fluorinated peptidomimetics under standard coupling conditions.

Application

N-Boc-4,4-difluoro-L-proline methyl ester serves as a conformationally constrained building block for peptide synthesis, leveraging the stereoelectronic effects of geminal difluorination to stabilize the Cγ-exo pseudoproline turn. The Boc group ensures stability and orthogonal deprotection, while the methyl ester facilitates downstream transformations. This derivative enables efficient incorporation into peptidomimetics and bioactive scaffolds, offering enhanced metabolic stability and defined backbone geometry in synthetic sequences.

General Information

CAS No. 203866-17-5
Cat. No. CS-W001497
Purity ≥98%
MDL No. MFCD03094918
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₁₇F₂NO₄
Molecular Weight 265.25
Synonym(s) 1,2-pyrrolidinedicarboxylic acid, 4,4-difluoro-, 1-(1,1-dimethylethyl) 2-methyl ester, (2S)-
SMILES COC(=O)[C@@H]1CC(CN1C(=O)OC(C)(C)C)(F)F

Computational Chemistry Data

TPSA 55.84
LogP 1.8041
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 1

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-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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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

Life Science Amino Acids and their Derivatives Proline and derivatives

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Amino Acid Derivatives

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N-Boc-4,4-difluoro-L-proline methyl ester

CAS No. 203866-17-5

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