118758-49-9 Usage
Uses
Used in Organic Chemistry:
(3S)-3-Phenyl-L-proline serves as a crucial building block in the synthesis of a wide array of pharmaceuticals and natural products. Its distinctive structure allows for the creation of complex molecules that can address specific medical needs.
Used in Asymmetric Synthesis:
As a potential catalyst, (3S)-3-Phenyl-L-proline has been explored for its use in asymmetric synthesis reactions. This application is significant as it can lead to the production of enantiomerically pure compounds, which are essential in the pharmaceutical industry to ensure the desired biological activity and minimize side effects.
Used in Catalyst and Ligand Development:
The chiral nature of (3S)-3-Phenyl-L-proline has sparked interest in its development as new chiral catalysts and ligands. These are vital for stereoselective processes, which are critical in producing specific enantiomers of chiral molecules, a key factor in the efficacy and safety of many drugs.
Used in the Generation of Bioactive Molecules:
(3S)-3-Phenyl-L-proline has demonstrated its potential as a versatile intermediate for creating diverse molecular structures with biological activity. This makes it a valuable component in the discovery and development of new drugs and therapeutic agents.
Check Digit Verification of cas no
The CAS Registry Mumber 118758-49-9 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,8,7,5 and 8 respectively; the second part has 2 digits, 4 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 118758-49:
(8*1)+(7*1)+(6*8)+(5*7)+(4*5)+(3*8)+(2*4)+(1*9)=159
159 % 10 = 9
So 118758-49-9 is a valid CAS Registry Number.
118758-49-9Relevant academic research and scientific papers
An efficient method for the stereoselective synthesis of cis-3-substituted prolines: Conformationally constrained α-amino acids
Flamant-Robin, Céline,Wang, Qian,Chiaroni, Angèle,Sasaki, N. André
, p. 10475 - 10484 (2007/10/03)
An efficient synthesis of enantiomerically pure cis-3-substituted prolines is reported. Key steps involve the stereoselective organocuprate addition to the (E)-α,β-unsaturated ester 1, obtained from the Garner's aldehyde, and expedient oxidation-cyclizati
Synthesis of Enantio- and Diastereoiso-merically Pure Substituted Prolines via Condensation of Glycine with Olefins Activated by a Carbonyl Group
Belokon', Yuri N.,Bulychev, Aleksandr G.,Pavlov, Viacheslav A.,Fedorova, Eugenia B.,Tsyryapkin, Vladimir A.,et al.
, p. 2075 - 2084 (2007/10/02)
The glycine fragment in the nickel(II) complex (1) formed from the Schiff's base of glycine and (S)-o-benzophenone (2) undergoes base-catalysed Michael addition to acrylaldehyde, α-methylacrylaldehyde, (E)-crotonaldehyde, (E)-cinnamaldehyde, and methyl vinyl ketone.No products of 1,2-addition were found in the Et3N-catalysed reactions.Addition followed by epimerization of the isomeric complexes proceeds with high diastereoselectivity at Cα (90percent) and Cβ of the corresponding amino acid side chains.After chromatographic separation, the diastereoisomerically pure complexes were decomposed and the resulting dihydropyrrole-2-carboxylic acids reduced with NaBH3CN to give (S)-proline, trans-3-methyl-(S)-proline, trans-5-phenyl-(S)-proline, and a mixture of cis- and trans-5-methyl-(S)-prolines.The chiral auxiliary (2) was recovered in 80-90percent yield.
