144072-87-7

Upstream product

• 106928-49-8 methyl (RS)-N-(benzyloxycarbonyl)-2-amino-4-pentenoate 
• 133773-64-5 (RS)-N-(benzyloxycarbonyl)-2-amino-4-pentenoic acid 
• 144073-07-4 (R)-2-{[1-Phenyl-meth-(Z)-ylidene]-amino}-pent-4-enoic acid amide 
• 127474-54-8 (R)-2-(benzyloxycarbonylamino)pent-4-enoic acid 
• 144073-06-3 α-allylglycine amide 
• 54594-06-8 D-allylglycine 
• 74-93-1 methylthiol 
• 127515-28-0 (R)-methyl 2-[N-(benzyloxycarbonyl)amino]-4-pentenoate 
• 501-53-1 benzyl chloroformate 
• 144072-88-8 methyl (RS)-N-(benzyloxycarbonyl)-2-amino-5-(acetylthio)pentanoate 
• 74-88-4 methyl iodide 

Relevant academic research and scientific papers

Synthesis of (Optically Active) Sulfur-Containing Trifunctional Amino Acids by Radical Addition to (Optically Active) Unsaturated Amino Acids

Sulfur-based radicals, generated from R-S-H-type precursors (R = alkyl, acyl) with AIBN, smoothly add to α-allylglycines protected at none, one, or both of the amino acid functions (NH2 and/or CO2H).Sulfur-containing trifunctional amino acids were obtained in good to excellent yields (64-100 percent).The solvent used for the reaction is critical.Optimal results were obtained when both the unsaturated amino acid and RSH dissolve completely in the medium (dioxane/water or methanol/water are good solvent systems).The scope of the reaction includes α-substituted α-allylglycine derivative and derivatives as well as β-substituted β-allyl-β-amino alcohols.In the case of optically active α-allylglycine derivatives, radical addition is accompanied by a small amount of racemization, the amount depending on the type of protection and R-S-H.The products are easily optically enriched by crystallization.Addition of sulfur-based radicals to α-allylglycine is believed to be an example of a general method for synthesizing optically active trifunctional amino acids from unsaturated amino acids.