182866-73-5

Upstream product

• 1149-26-4 (S)-N-(benzyloxycarbonyl)valine 
• 119153-86-5 C₁₆H₂₁NO₆ 
• 13139-28-1 (S)-N-benzyloxycarbonylvalinamide 
• 24762-04-7 2-Diazo-3-oxo-butyric acid methyl ester 
• 182866-65-5 methyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-methylbutanamido)-3-oxobutanoate 
• 145587-61-7 (4S,5S)-2-((1S)-1-benzyloxycarbonylamino-2-methylpropyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester 

Downstream Products

• 203782-26-7 2-((S)-1-Benzyloxycarbonylamino-2-methyl-propyl)-5-methyl-oxazole-4-carboxylic acid 
• 203782-30-3 2-{[2-((S)-1-Benzyloxycarbonylamino-2-methyl-propyl)-5-methyl-oxazole-4-carbonyl]-amino}-3-oxo-butyric acid methyl ester 
• 203782-28-9 [(S)-1-(4-Carbamoyl-5-methyl-oxazol-2-yl)-2-methyl-propyl]-carbamic acid benzyl ester 
• 303041-82-9 (1-{4-[2-(1H-indol-3-yl)-ethylcarbamoyl]-5-methyl-oxazol-2-yl}-2-methyl-propyl)-carbamic acid benzyl ester 

Relevant academic research and scientific papers

Rapid synthesis of oxazoles under microwave conditions

A new and efficient variation of the Robinson-Gabriel oxazole synthesis is described. Oxazoles were prepared by cyclodehydration of 2-acylamino carbonyl compounds with Burgess reagent under monomode microwave irradiation.

A New Synthesis of Highly Functionalized Oxazoles

Functionalized oxazoles and bis-oxazoles are obtained by side-chain oxidation of β-hydroxy amides with the Dess-Martin periodinane, followed by cyclodehydration with triphenylphosphine/iodine in the presence of triethylamine.

Studies towards the synthesis of diazonamide A. Synthesis of the indole bis-oxazole fragment

The indole bis-oxazole 2, a potential intermediate for the synthesis of the marine natural product diazonamide A 1, has been synthesised, and attempts to construct the model macrocycle (ring B) 3 are also described; in both approaches rhodium carbenoid N-H insertion reactions are used in key steps. (C) 2000 Elsevier Science Ltd.

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.