88636-83-3

Upstream product

• 75-44-5 phosgene 
• 6335-76-8 3-amino-3-phenylpropionic acid ethyl ester 
• 945419-93-2 C₁₄H₂₃O₂NSi 
• 29754-04-9 ethyl 3-amino-3-phenylpropanoate hydrochloride 
• 3646-50-2 3-Amino-3-phenylpropionic acid 
• 1021464-42-5 ethyl 3-phenyl-3-(trimethylsiloxycarbonylamino)propanoate 

Downstream Products

• 92653-05-9 (+/-)-3-Diacetylamino-3-phenyl-propionsaeureaethylester 
• 93142-96-2 (+/-)-3-<3-Butyl-ureido>-3-phenyl-propionsaeureaethylester 
• 403608-54-8 C₂₁H₃₃N₃O₅ 
• 671197-35-6 C₃₂H₃₉N₅O₅ 

Relevant academic research and scientific papers

Organosilicon synthesis of isocyanates: IV. Synthesis of isocyanates from aliphatic and alkylaromatic amino acid esters

Treatment of an alcoholic suspension of amino acids with trimethylchlorosilane yielded phenylglycine, valine, β-phenylalanine, and homovaline ester hydrochlorides. Their saccharin-catalyzed silylation with hexamethyldisilazane proceeds quantitatively and involves only one proton of the amino group. The best conversion of the amino acid esters to the corresponding isocyanates was achieved by phosgene treatment of their monosilyl urethanes, rather than of the silylated amino esters. Monosilyl urethanes are formed quantitatively by treatment of the amino acid ester hydrochlorides with the hexamethyldisilazane-CO2 system. The 1H NMR spectra show that monosilyl urethanes derived from α-and β-amino acid esters are characterized by intramolecular interaction of the silicon atom and the oxygen atom of the carboxy group. Nauka/Interperiodica 2007.

Organosilicon synthesis of isocyanates: III. Synthesis of aliphatic, carbocyclic, aromatic, and alkylaromatic isocyanatocatboxylic acid esters

A series of aminoacid esters was prepared by treating the aminoacid suspensions in ethanol with thionyl chloride. Best conversion of aminoacid esters to corresponding isocyanates was achieved in the case of aromatic and carbocyclic aminoesters by phosgeneation of their N-silyl derivatives, and in the case of aliphatic and alkylaromatic aminoesters by phosgeneation of O-silyl or N,O-bissilylurethanes on their basis. In the last case additional step of esterification of the by-products isocyanatoalkylcarboxylic acid chlorides is required after phosgeneation. Unusual generation of cynnamates and intramolecular N→O-migration of trimethylsilyl group in the solutions of silylated alkylaromatic β-aminoacid esters were found. Pleiades Publishing, Inc., 2006.

Design and synthesis of potent and selective inhibitors of integrin VLA-4

The synthesis and identification of a novel series of inhibitors of integrin VLA-4 are described. Their in vitro activity and selectivity against closely related integrins are also presented.