220717-55-5

Upstream product

• 145587-61-7 (4S,5S)-2-((1S)-1-benzyloxycarbonylamino-2-methylpropyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester 
• 267653-10-1 (4R,5R)-2-((S)-1-Benzyloxycarbonylamino-2-methyl-propyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester 
• 145587-62-8 (4S,5R)-2-((1S)-1-benzyloxycarbonylamino-2-methylpropyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester 

Downstream Products

• 610320-39-3 2-((R)-1-{[(4S,5R)-2-((S)-1-Benzyloxycarbonylamino-2-methyl-propyl)-5-methyl-4,5-dihydro-oxazole-4-carbonyl]-amino}-2-methyl-propyl)-1,5-dimethyl-1H-imidazole-4-carboxylic acid benzyl ester 
• 220717-68-0 2-((S)-1-{[2-((S)-1-{[(4S,5R)-2-((S)-1-Benzyloxycarbonylamino-2-methyl-propyl)-5-methyl-4,5-dihydro-oxazole-4-carbonyl]-amino}-2-methyl-propyl)-oxazole-4-carbonyl]-amino}-2-methyl-propyl)-thiazole-4-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Total synthesis of bistratamide D

The total synthesis of the macrocyclic hexapeptide bistratamide D is reported. The synthetic strategy involved assembly of enantiomerically pure oxazole, thiazole, and oxazoline segments derived from amino acids. Macrocyclization of the hexapeptidic aminooxazoline-oxazole-thiazole carboxylic acid fragment was accomplished by activation with O-(7- azabenzotriazol-1-yl)-N,N,N',N'-tetramethyl-uronium hexafluorophosphate (HATU).

Synthesis of cyclopeptide alkaloids by cyclooligomerization of dipeptidyl oxazolines

Cyclodehydration of Cbz-valylthreonine methyl esters with Burgess reagent provides access to cis- and trans-oxazoline segments for cyclooligomerization reactions. The ratio of 12-, 18-, 24-, and larger-ring macrocycles obtained in this process is kinetica