80182-99-6

Basic information

• Product Name: Phenylalanine, b-hydroxy-, methyl ester, hydrochloride
• CAS NO: 80182-99-6
• Molecular Formula: C10H13NO3.ClH
• Molecular Weight: 231.679
• Mol File: 80182-99-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Phenylalanine, b-hydroxy-, methyl ester, hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Phenylalanine, b-hydroxy-, methyl ester, hydrochloride(80182-99-6)
• EPA Substance Registry System: Phenylalanine, b-hydroxy-, methyl ester, hydrochloride(80182-99-6)

Safety Data

• Hazardous Substances Data: 80182-99-6(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 67-56-1 methanol 
• 69-96-5 Phenylserin 
• 38061-23-3 α-Phenylacyl amino acid methyl ester hydrochloride 
• 69-96-5 (2RS,3RS)-2-amino-3-hydroxy-3-phenyl-propionic acid 

Downstream Products

• 109924-96-1 Ac-(R,S)-Phe-(R,S)-PhSer-OMe 
• 19185-84-3 (2SR,3SR)-N-benzoyl-β-phenylserine methyl ester 
• 19185-84-3 N-benzoyl-β-phenylserine methyl ester 
• 100020-81-3 β-chloro-β-phenylalanine methyl ester hydrochloride 
• 106111-12-0 Z-Gly-PhSer-OMe 
• 17193-36-1 (2S*,3R*)-2-tert-butoxycarbonylamino-3-hydroxy-3-phenyl-propionic acid methyl ester 
• 17193-36-1 (±)-(2R,3R)-2-tert-butoxycarbonylamino-3-hydroxy-3-phenylpropionic acid methyl ester 
• 69-96-5 (2RS,3RS)-2-amino-3-hydroxy-3-phenyl-propionic acid 
• 55478-15-4 methyl (S,Z)-2-(2-((tert-butoxycarbonyl)amino)propanamido)-3-phenylacrylate 

Relevant articles and documents

Cyclizing pentapeptides: Mechanism and application of dehydrophenylalanine as a traceless turn-inducer

Dehydrophenylalanine is used as a traceless turn-inducer in the total synthesis of dichotomin E. Macrocyclization of the monomer is achieved in high yields and selectivity over cyclodimerization under conditions 100 times more concentrated than previously achieved. The enamide facilitates ring closing, and Rh-catalyzed hydrogenation of the unsaturated cyclic peptide results in selective formation of the natural product or its epimer, depending on our choice of phosphine ligand. NMR analysis and molecular modeling revealed that the linear peptide adopts a left-handed α-turn that preorganizes the N- and C-termini toward macrocyclization.

Asymmetric transfer hydrogenation of α-amino β-keto ester hydrochlorides through dynamic kinetic resolution

The development of Ru-catalyzed asymmetric transfer hydrogenation of α-amino β-keto ester hydrochlorides is described. The reaction proceeds through dynamic kinetic resolution to afford anti β-hydroxy α-amino esters with good diastereomeric ratios and high enantioselectivities.

Nitrate esters in the generation of amino acid radicals

Nitrate esters, prepared by treatment of β-hydroxy-α-amino acid derivatives with nitric acid, react with tributyltin hydride to give the corresponding alkoxyl radicals. These radicals readily undergo β-scission, providing a convenient route for the regiocontrolled production of α-carbon-centred amino acid radicals. By examining the partitioning of the alkoxyl radicals between the β-scission process and the competing hydrogen transfer reaction, it has been possible to evaluate the influence of electronic and steric effects on the β-scission reaction and the formation of the carbon-centred radicals.