220438-32-4

Upstream product

• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 2344-80-1 Chloromethyltrimethylsilane 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 

Downstream Products

• 429685-00-7 3-phenyl-2-{[2-(2,2,2-trifluoroacetylamino)acetyl]trimethylsilylmethylamino}propionic acid methyl ester 
• 429684-98-0 2-[(2-tert-butoxycarbonylamino-3-hydroxypropionyl)trimethylsilylmethylamino]-3-phenylpropionic acid methyl ester 
• 609347-77-5 2-[(2-tert-butoxycarbonylaminoacetyl)trimethylsilylmethylamino]-3-phenylpropionic acid methyl ester 
• 1027294-96-7 3-phenyl-2-((phenylacetyl)(trimethylsilanylmethyl)amino)propionic acid methyl ester 
• 90788-17-3 DL-methyl 2-<(dimethylamino)methyl>-3-phenylpropionate 
• 103-26-4 Methyl cinnamate 

Relevant academic research and scientific papers

Accessing Aliphatic Amines in C-C Cross-Couplings by Visible Light/Nickel Dual Catalysis

A general aminoalkylation of aryl halides was developed, overcoming intolerance of free amines in nickel-mediated C-C coupling. This transformation features broad functional group tolerance and high efficiency. Taking advantage of the fast desilylation of α-silylamines upon single-electron transfer (SET) facilitated by carbonate, α-amino radicals are generated regioselectively, which then engage in nickel-mediated C-C coupling. The reaction displays high chemoselectivity for C-C over C-N bond formation. Highly functionalized pharmacophores and peptides are also amenable.

Multifunctional Building Blocks Compatible with Photoredox-Mediated Alkylation for DNA-Encoded Library Synthesis

DNA-encoded library (DEL) technology has emerged as a novel interrogation modality for ligand discovery in the pharmaceutical industry. Given the increasing demand for a higher proportion of C(sp3)-hybridized centers in DEL platforms, a photore

Building addressable libraries: Site-selective formation of an N-acyliminium ion intermediate

(Chemical Equation Presented) A strategy for site-selectively generating reactive N-acyliminium ion intermediates on a microelectrode array has been developed. The route capitalizes on the use of an electroauxiliary for building a methoxylated amino acid

Building functionalized peptidomimetics: Use of electroauxiliaries for introducing N-acyliminium ions into peptides

A series of silyl-substituted amino acids have been synthesized, inserted into peptides, and then employed as precursors for oxidatively generating reactive N-acyliminium ions. Both electrochemical and chemical oxidation procedures have been employed. N-Acyliminium ion generation in a solid-phase substrate as well as application to a small library of functionalized dipeptides has been demonstrated. Limitations in terms of how electron-rich the silyl groups can be as well as the compatibility of multiple silyl groups within a longer peptide are defined.

Building functionalized peptidomimetics: New electroauxiliaries and the use of a chemical oxidant for introducing N-acyliminium ions into peptides

(Matrix presented) The removal of electroauxiliaries from peptide substrates with chemical oxidants has been examined as a method for inserting N-acyliminium ions into the peptides. To this end, it was found that both 4-methoxyphenyldimethylsilyl and 2,4-

Silyl-Substituted Amino Acids: New Routes to the Construction of Selectively Functionalized Peptidomimetics

(matrix presented) Silylated amino acids have been incorporated into peptides and then converted into N-acyliminium ions with the use of an anodic oxidation reaction. The result is a method for selectively incorporating conformational constraints or exter

Novel isomerization reaction of N,N-dimethyl-α-(methoxycarbonyl)-4- substituted-benzylammonium N-methylides

Fluoride ion-induced desilylation of N,N-dimethyl-N- [(trimethylsilyl)methyl]-α-(methoxycarbonyl)4-substituted benzylammonium salts (7) gave two Stevens rearrangement products: methyl 3-(dimethylamino)- 2-(4-substituted phenyl)propionates (13) from N-methylides 8, and methyl 3- (dimethylamino)-3-(4-substituted phenyl)propionates (15) from N-benzylides 10. Additional Stevens rearrangement products, methyl 2-(dimethylamino)-3- (4-substituted phenyl)propionates (16), were competitively formed from ylides 12 when the cesium fluoride used was not predried. The mechanism of the isomerization from methylides 8, which was initially generated, to 10 and 12 is discussed.