104241-40-9

Upstream product

• 104241-23-8 (2S,3S,4S)-2-(tert-butoxycarbonyl)amino-3-hydroxy-4-methyl-5-benzyloxypentanoic acid methyl ester 

Downstream Products

• 106391-79-1 N-(benzyloxycarbonyl)-O-(tert-butyldimethylsilyl)-L-threonyl-4(R)-hydroxy-L-prolyl-3(R)-hydroxy-L-homotyrosinyl-L-threonyl-3(S)-hydroxy-4(S)-methyl-L-proline amide 
• 104197-66-2 (2S,3S,4S)-3-Hydroxy-4-methyl-pyrrolidine-2-carboxylic acid methyl ester 
• 71018-13-8 echinocandin D 
• 104213-53-8 N-(benzyloxycarbonyl)-O-(tert-butyldimethylsilyl)-L-threonyl-4(R)-hydroxy-L-prolyl-3(R)-hydroxy-L-homotyrosinyl-L-threonyl-3(S)-hydroxy-4(S)-methyl-L-proline methyl ester 

Relevant academic research and scientific papers

Synthetic Studies on Antifungal Cyclic Peptides, Echinocandins. Stereoselective Total Synthesis of Echinocandin D via a Novel Peptide Coupling

Synthetic studies on the novel fungicidal oligopeptides, echinocandins (1b and 1c), are described.The constituent amino acids 5-8 were synthesized in a stereocontrolled manner from the chiral starting materials, 5a, 6a and 7a, respectively.The coupling of these amino acids was characterized by the use of unprotected amino acid as the C-terminal and 2-pyridyl thiol ester as the N-terminal, and the coupling was performed in the presence of 1-(trimethylsilyl)imidazole (TMSIm) or a catalytic amount of tert-amine to give C-terminal free dipeptides, 14 and 16a, respectively, which were converted to the pentapeptide 17a, a common intermediate for the synthesis of 1b and 1c.The synthesis of 1c was achieved by the cyclization of the hexapeptide 24b.