128946-58-7

Upstream product

• 611-71-2 (R)-Mandelic Acid 
• 111556-22-0 (-)-(R)-2-(2-Hydroxy-2-phenylacetamido)-N,N,2-trimethylpropionamid 

Downstream Products

• 128858-22-0 2-Methyl-2-[(R)-2-phenyl-2-(tetrahydro-pyran-2-yloxy)-acetylamino]-propionic acid 
• 128858-23-1 2-Methyl-2-[(R)-2-phenyl-2-(tetrahydro-pyran-2-yloxy)-acetylamino]-propionic acid (R)-(1-dimethylcarbamoyl-1-methyl-ethylcarbamoyl)-phenyl-methyl ester 
• 128858-24-2 (-)-(R,R)-2-(2-<2-(2-Hydroxy-2-phenylacetamido)-2-methylpropionato>-2-phenylacetamido)-N,N,2-trimethylpropionamid 
• 128858-29-7 (-)-(R,R)-3,3,9,9-Tetramethyl-6,12-diphenyl-1,7-dioxa-4,10-diazacyclododecan-2,5,8,11-tetron 

Relevant academic research and scientific papers

Synthese cyclischer Depsipeptide durch direkte Amid-Cyclisierung: 12gliedrige Depsipeptide mit alternierender Sequenz von α-Hydroxy- und α-Aminosaeuren

Synthesis of Cyclic Depsipeptides via Direct Amide Cyclization: Cyclic Depsipeptides with 12-Ring Atoms and Alternating Sequence of α-Hydroxy and α-Amino Acids - - The reaction of 3-(dimethylamino)-2,2-dimethyl-2H-azirine (1; R1=R2=R3=R4=Me) with α-hydroxycarboxylic acids, followed by selective hydrolysis of the terminal dimethylamide group yields the dipeptide analogues 15a and 18b (Schemes 3 and 4).After protection of the OH group (-> 16a and 19, resp.), coupling with the C-terminus-protected derivatives 14 and 18a, respectively, by a modified 1,1'-carbonyldiimidazole procedure followed by hydrolysis gives the linear depsipeptides 17c and 20, respectively.Treatment with HCl gas in toluene at 100 deg C leads to the cyclic depsipeptides 21 and 22 in very good yield.The two model reactions show that the 'azirine/oxazolone-method', combined with the 'direct amide cyclization' is a versatile procedure for the synthesis of cyclic depsipeptides containing α,α-disubstituted α-amino acids.