Boc-D-Phe(3-CF3)-OH

Name: Boc-D-Phe(3-CF3)-OH
Brand: ChemScene
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CAS No. 82317-82-6
Cat. No. CS-W014501
Molecule weight333.30
Purity≥98%
MDL No.MFCD00672525

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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+
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Structure of 82317-82-6

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General Information

CAS No. 82317-82-6
Cat. No. CS-W014501
Purity ≥98%
MDL No. MFCD00672525
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₅H₁₈F₃NO₄
Molecular Weight 333.30
Synonym(s) None
SMILES O=C([C@@H](CC1=CC=CC(C(F)(F)F)=C1)NC(OC(C)(C)C)=O)O

Description

Boc-D-Phe(3-CF3)-OH features a trifluoromethyl-substituted phenylalanine residue with a robust Boc protecting group, enabling stable incorporation into peptide chains. The electron-withdrawing trifluoromethyl group enhances metabolic stability and modulates electronic properties in synthetic sequences. This bench-stable derivative facilitates efficient coupling reactions under standard conditions.

Application

Boc-D-Phe(3-CF₃)-OH serves as a valuable building block for the synthesis of D-amino acid-containing peptides and bioactive molecules. The 3-trifluoromethylphenyl group imparts enhanced metabolic stability and lipophilicity, while the Boc protecting group ensures facile deprotection under mild acidic conditions. This derivative enables efficient incorporation of D-Phe into peptide scaffolds with improved pharmacokinetic properties, particularly in medicinal chemistry campaigns targeting protease-resistant analogs.

Synthesis

Route1
- In-stock
  
  24424-99-5
- 82317-79-1
- ~89%
- In-stock
  
  82317-82-6
References
- Nestor Jr.; Ho; Simpson; Horner; Jones; McRae; Vickery Journal of Medicinal Chemistry, 1982 , vol. 25, # 7 p. 795 - 801
Route2
- 82337-57-3
- ~%
- In-stock
  
  82317-82-6
References
- Journal of Medicinal Chemistry, , vol. 25, # 7 p. 795 - 801
Route3
- 21172-44-1
- ~%
- In-stock
  
  82317-82-6
References
- Journal of Medicinal Chemistry, , vol. 25, # 7 p. 795 - 801

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

Quality Control

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Computational Chemistry Data

TPSA 75.63
LogP 3.2258
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 4

Other Classifications

Bioactive Molecules Peptides

Life Science Amino Acids and their Derivatives Phenylalanine and derivatives

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

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Boc-D-Phe(3-CF3)-OH

CAS No. 82317-82-6

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