182866-72-4

Upstream product

• 13139-27-0 L-α-N-Cbz-alaninamide 
• 65638-93-9 N-Carbobenzoxy-L-alanin-kohlensaeureaethylesteranhydrid 
• 1142-20-7 N-Cbz-Ala 
• 24762-04-7 2-Diazo-3-oxo-butyric acid methyl ester 
• 182866-64-4 2'(S)-2-(2-benzyloxycarbonylaminopropionylamino)-3-oxobutyric acid methyl ester 

Downstream Products

• 186453-48-5 2-((S)-1-{[2-((R)-1-{[2-(tert-Butoxycarbonylamino-methyl)-thiazole-4-carbonyl]-amino}-2-methyl-propyl)-thiazole-4-carbonyl]-amino}-ethyl)-5-methyl-oxazole-4-carboxylic acid pentafluorophenyl ester 
• 521096-62-8 1'(R)-2-(1-{[1'(R)-2-(1-{[1'(S)-2-(1-benzyloxycarbonylaminoethyl)-5-methyloxazole-4-carbonyl]amino}-2-methylpropyl)thiazole-4-carbonyl]amino}-2-methylproplyl)thiazole-4-carboxylic acid ethyl ester 
• 521096-57-1 1'(R)-2-(1-{[1'(S)-2-(1-benzyloxycarbonylaminoethyl)-5-methyloxazole-4-carbonyl]amino}-2-methylpropyl)thiazole-4-carboxylic acid ethyl ester 
• 521096-61-7 1'(R)-2-(1-{[1'(S)-2-(1-benzyloxycarbonylaminoethyl)-5-methyloxazole-4-carbonyl]amino}-2-methylpropyl)thiazole-4-carboxylic acid 
• 521096-39-9 1'(S)-2-(1-benzyloxycarbonylaminoethyl)-5-methyloxazole-4-carboxylic acid 

Relevant academic research and scientific papers

Dendroamide A, nostocyclamide and related cyclopeptides from cyanobacteria. Total synthesis, together with organised and metal-templated assembly from oxazole and thiazole-based amino acids

Oxazole and thiazole-based amino acids (15-18) are shown to undergo organised and metal-templated assemblies leading to novel cyclic peptides. Thus, a 1:1:1 mixture of the amino acids (15, 16 and 17) undergo cyclisation in the presence of FDPP producing t

Synthesis of functionalised oxazoles and bis-oxazoles

A new method for the synthesis of oxazoles, and in particular chiral non-racemic oxazoles derived from amino acids, has been developed. Thus, rhodium(II) catalysed reaction of diazocarbonyl compounds 6 and 11 in the presence of amides 8 and 10 results in regioselective insertion of the carbenoid into the amide N-H bond with formation of the β-carbonyl amides 9 and 12. Cyclodehydration of amides 9 and 12 using triphenylphosphine-iodine-triethylamine gives functionalised oxazoles 7 and 13. The oxazoles 13c and 13f were converted into the bis-oxazoles 17a and 17b by a second rhodium(II) catalysed regioselective N-H insertion reaction on the amides 15, followed by cyclodehydration.