1365570-76-8

Upstream product

• 63-91-2 L-phenylalanine 
• 198008-33-2 C₁₄H₁₈Br₂O₃ 
• 1365570-63-3 C₂₃H₂₈BrNO₅ 
• 106-96-7 propargyl bromide 

Downstream Products

• 1369377-74-1 (S)-(1-hexyl-1H-1,2,3-triazol-4-yl)methyl 2-((S)-4-bromo-5-oxo-2-((1S,2R,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl-oxy)-2,5-dihydrofuran-3-ylamino)-3-phenylpropanoate 
• 1369377-58-1 (S)-(1-benzyl-1H-1,2,3-triazol-4-yl)methyl 2-((S)-4-bromo-5-oxo-2-((1S,2R,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yloxy)-2,5-dihydrofuran-3-ylamino)-3-phenylpropanoate 

Relevant academic research and scientific papers

Concise synthesis of chiral 2(5H)-furanone derivatives possessing 1,2,3-triazole moiety via one-pot approach

Combining three bioactive units, such as 2(5H)-furanone, 1,2,3-triazole, and amino acid together into one potential drug molecule with polyfunctional groups, a series of new chiral 2(5H)-furanone derivatives containing 1,2,3-triazole moiety have been designed and synthesized from (5S)-5-alkoxy-3,4-dibromo-2(5H)-furanones, amino acids, propargyl bromide, and organic azides via the sequential three steps, including asymmetric Michael addition-elimination, substitution, and click reaction. The latter two steps, substitution and click reaction could proceed smoothly in a one-pot process. Furthermore, the target products could be directly synthesized via a four-component one-pot approach.

Synthesis of N-[5-alkoxy-2(5H)-furanonyl] amino acid propargyl esters

Using K2CO3 as a base and CH3CN as solvent, different kinds of N-[5-alkoxy-2(5H)-furanonyl] amino acids were reacted with propargyl bromide via substitution reaction at 40 °C to give 16 N-[5-alkoxy-2(5H)-furanonyl] amino acid propargyl esters with the yields of 44-85% (mostly over 74%). The structures of all newly synthesized compounds were elucidated and confirmed by FTIR, UV, 1H NMR, C NMR, MS, and elemental analysis. The rapid, efficient, and brief synthesis of the series propargyl esters with multiple bioactive units, will afford not only a basis for the activity test of potential drug molecules, but also an important synthetic strategy for 2(5H)-furanone derivatives with polyfunctional groups. Springer Science+Business Media B.V. 2011.