Boc-D-3,5-Difluorophenylalanine

Name: Boc-D-3,5-Difluorophenylalanine
Brand: ChemScene
Availability: InStock
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CAS No. 205445-53-0
Cat. No. CS-0154580
Purity≥98%
MDL No.MFCD00797556

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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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Boc-D-3,5-Difluorophenylalanine|CS-0154580

Structure of 205445-53-0

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General Information

CAS No. 205445-53-0
Cat. No. CS-0154580
Purity ≥98%
MDL No. MFCD00797556
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₁₇F₂NO₄
Molecular Weight 301.29
Synonym(s) N-(tert-butoxycarbonyl)-3,5-difluoro-D-phenylalanine
SMILES CC(C)(OC(N[C@@H](C(O)=O)CC1=CC(F)=CC(F)=C1)=O)C

Description

Boc-D-3,5-Difluorophenylalanine features a sterically hindered, electron-deficient phenyl ring stabilized by two fluorine substituents at the 3 and 5 positions. This configuration enhances metabolic stability and influences conformational preferences in peptide backbones. The Boc protecting group enables straightforward incorporation into solid-phase synthesis workflows.

Application

Boc-D-3,5-Difluorophenylalanine serves as a valuable chiral building block for the synthesis of fluorinated peptide scaffolds and bioactive compounds. The Boc group provides excellent stability and ease of removal under mild acidic conditions, while the 3,5-difluoro substitution enhances metabolic stability and modulates electronic properties. This derivative facilitates efficient coupling reactions and is compatible with standard solid-phase and solution-phase peptide synthesis workflows.

Synthesis

Route1
- 1246400-77-0
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  205445-53-0
References
- Bioorganic and Medicinal Chemistry Letters, , vol. 20, # 19 p. 5607 - 5612

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 75.63
LogP 2.4852
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 4

Other Classifications

Building Blocks Functional Group Boc

Building Blocks Functional Group Fluoride

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

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Boc-D-3,5-Difluorophenylalanine

CAS No. 205445-53-0

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