Tosyl-D-phenylalanine

Name: Tosyl-D-phenylalanine
Brand: ChemScene
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CAS No. 86117-53-5
Cat. No. CS-0169311
Molecule weight319.38
Purity≥98%
MDL No.None

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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+
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General Information

CAS No. 86117-53-5
Cat. No. CS-0169311
Purity ≥98%
MDL No. None
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₆H₁₇NO₄S
Molecular Weight 319.38
Synonym(s) N-Tosyl-D-phenylalanine
SMILES O=C(O)[C@@H](CC1=CC=CC=C1)NS(=O)(C2=CC=C(C)C=C2)=O

Description

Tosyl-D-phenylalanine serves as a chiral building block for peptide synthesis, offering enhanced solubility and stability. The tosyl group facilitates efficient activation and coupling under standard conditions, while the D-configuration provides stereochemical control in complex peptide architectures.

Application

Tosyl-D-phenylalanine serves as a stable, bench-ready chiral building block for peptide synthesis and medicinal chemistry applications. The tosyl group provides excellent protection for the amine functionality, enabling orthogonal deprotection strategies. It exhibits high functional group tolerance and facilitates efficient coupling reactions under standard conditions. This derivative supports scalable synthesis of D-amino acid-containing peptides and is well-suited for use in API development workflows requiring stereochemical control.

Synthesis

Route1
- In-stock
  
  673-06-3
- 98-59-9
- ~79%
- In-stock
  
  86117-53-5
References
- Storer, R. Ian; Takemoto, Toshiyasu; Jackson, Philip S.; Brown, Dearg S.; Baxendale, Ian R.; Ley, Steven V. Chemistry - A European Journal, 2004 , vol. 10, # 10 p. 2529 - 2547

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 83.47
LogP 1.96922
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 6

Other Classifications

Building Blocks Functional Group Carboxylic Acid

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Life Science Amino Acids and their Derivatives Phenylalanine and derivatives

Chemical Biology Peptide Chemistry Amino Acid Derivatives

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Tosyl-D-phenylalanine

CAS No. 86117-53-5

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