252554-79-3

Basic information

• Product Name: (4S,5R)-3-(FMOC-ALA)-2,2,5-TRIMETHYL-OXAZOLIDINE-4-CARBOXYLIC ACID
• Synonyms: FMOC-ALA-THR(PSI(ME,ME)PRO)-OH;(4S,5R)-3-(FMOC-ALA)-2,2,5-TRIMETHYL-OXAZOLIDINE-4-CARBOXYLIC ACID;(4S,5R)-3-(Fmoc-Ala)-2,2,5-trimethyl-oxazolidine-4;(4S,5R)-3-(Fmoc-Alaninyl)-2,2,5-trimethyloxazolidine-4-carboxylic acid;Fmoc-Ala-Thr(ΨMe,Me pro)-OH;Fmoc-L-Ala-L-Thr[PSI(Me,Me)Pro]-OH;Fmoc-Ala-Thr(psi(Me,Me))-OH;(9H-Fluoren-9-yl)MethOxy]Carbonyl Ala-ThrPsi(Me,Me)Pro-OH
• CAS NO: 252554-79-3
• Molecular Formula: C25H28N2O6
• Molecular Weight: 452.5
• Product Categories: peptide
• Mol File: 252554-79-3.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 681.2±55.0 °C(Predicted)
• Appearance: /
• Density: 1.259±0.06 g/cm3(Predicted)
• Storage Temp.: -15°C
• PKA: 3.15±0.60(Predicted)
• CAS DataBase Reference: (4S,5R)-3-(FMOC-ALA)-2,2,5-TRIMETHYL-OXAZOLIDINE-4-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (4S,5R)-3-(FMOC-ALA)-2,2,5-TRIMETHYL-OXAZOLIDINE-4-CARBOXYLIC ACID(252554-79-3)
• EPA Substance Registry System: (4S,5R)-3-(FMOC-ALA)-2,2,5-TRIMETHYL-OXAZOLIDINE-4-CARBOXYLIC ACID(252554-79-3)

Safety Data

• Hazardous Substances Data: 252554-79-3(Hazardous Substances Data)

Usage

Description

(4S,5R)-3-(FMOC-ALA)-2,2,5-TRIMETHYL-OXAZOLIDINE-4-CARBOXYLIC ACID is a chiral derivative of oxazolidine carboxylic acid, characterized by its molecular formula C18H27NO5 and a molecular weight of 333.41 g/mol. (4S,5R)-3-(FMOC-ALA)-2,2,5-TRIMETHYL-OXAZOLIDINE-4-CARBOXYLIC ACID features a 3-(FMOC-ALA) group attached to a cyclic oxazolidine ring, which is further complemented by a carboxylic acid functional group. Its unique structure and chirality make it a versatile building block in organic synthesis and pharmaceutical research, suitable for the development of novel compounds and drug molecules.

Uses

Used in Pharmaceutical Research:
(4S,5R)-3-(FMOC-ALA)-2,2,5-TRIMETHYL-OXAZOLIDINE-4-CARBOXYLIC ACID is used as a key intermediate in the synthesis of pharmaceutical compounds, particularly for the development of new drugs. Its chiral nature and functional groups allow for the creation of enantioselective reactions and the formation of complex molecular structures with potential therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, (4S,5R)-3-(FMOC-ALA)-2,2,5-TRIMETHYL-OXAZOLIDINE-4-CARBOXYLIC ACID serves as a valuable building block for the construction of various organic molecules. Its cyclic oxazolidine ring and carboxylic acid group provide opportunities for further functionalization and the creation of diverse chemical entities with potential applications in materials science, agrochemicals, and other areas.
Used in Chiral Chemistry:
(4S,5R)-3-(FMOC-ALA)-2,2,5-TRIMETHYL-OXAZOLIDINE-4-CARBOXYLIC ACID is utilized as a chiral auxiliary in asymmetric synthesis, enabling the selective formation of enantiomerically pure compounds. Its presence can influence the stereochemistry of reactions, leading to the production of desired enantiomers with high selectivity, which is crucial for the development of enantioselective catalysts and chiral ligands.
Used in Drug Development:
In the drug development industry, (4S,5R)-3-(FMOC-ALA)-2,2,5-TRIMETHYL-OXAZOLIDINE-4-CARBOXYLIC ACID is employed as a precursor for the synthesis of potential drug candidates. Its unique structure can be modified to incorporate various pharmacophores, leading to the discovery of new therapeutic agents with improved efficacy, selectivity, and safety profiles.

Relevant articles and documents

Pseudo-Prolines in Peptide Synthesis: Direct Insertion of Serine and Threonine Derived Oxazolidines in Dipeptides

Dipeptides containing serine and threonine derived oxazolidines are prepared by reacting side chain unprotected dipeptides containing C-terminal Thr or Ser with dimethoxypropane.The resulting building blocks can be coupled in Fmoc-based solid phase peptide synthesis enhancing peptide solvation by its secondary structure disrupting potential.The present procedure may be considered as a first step towards a reversible modification of structural and functional properties of bioactive peptides and proteins.