177747-27-2

Upstream product

• 98210-50-5 Z-Ser(Bu^t)-Val-OH 
• 177747-22-7 methyl N-(2,2-dimethyl-2H-azirin-3-yl)-L-prolinate 
• 147-85-3 L-proline 
• 177747-26-1 (S)-2-((S)-2-Benzyloxycarbonylamino-3-tert-butoxy-propionylamino)-3-methyl-butyric acid methyl ester 
• 177747-24-9 (S)-1-(2-Methyl-thiopropionyl)-pyrrolidine-2-carboxylic acid methyl ester 
• 177747-23-8 (S)-methyl 1-(isobutyryl)pyrrolidine-2-carboxylate 
• 6306-52-1 L-valine methylester hydrochloride 
• 1676-75-1 N-benzyloxycarbonyl-O-t-butyl-L-serine 

Downstream Products

• 177747-31-8 Z-Ser(t-Bu)-Val-Aib-Pro-Aib-Leu-Aib-Pro-Leuol 
• 177747-29-4 {(S)-2-tert-Butoxy-1-[(S)-1-(1,1-dimethyl-2-{(S)-2-[1-methyl-1-(methyl-phenyl-carbamoyl)-ethylcarbamoyl]-pyrrolidin-1-yl}-2-oxo-ethylcarbamoyl)-2-methyl-propylcarbamoyl]-ethyl}-carbamic acid benzyl ester 
• 177747-30-7 2-[((S)-1-{2-[(S)-2-((S)-2-Benzyloxycarbonylamino-3-tert-butoxy-propionylamino)-3-methyl-butyrylamino]-2-methyl-propionyl}-pyrrolidine-2-carbonyl)-amino]-2-methyl-propionic acid 
• 177747-28-3 (S)-1-{2-[(S)-2-((S)-2-Benzyloxycarbonylamino-3-tert-butoxy-propionylamino)-3-methyl-butyrylamino]-2-methyl-propionyl}-pyrrolidine-2-carboxylic acid 

Relevant academic research and scientific papers

A new 3-amino-2H-azirine as an Aib-Pro synthon: Synthesis of the C-terminal nonapeptide of trichovirin I 1B

The synthesis of methyl N-(2,2-dimethyl-2H-azirin-3-yl)-L-prolinate (3), a novel 3-amino-2H-azirine, is described. It is shown that the reaction of COCl2 with thioamide 5 is remarkably faster than with the corresponding amide 4, and the yield of 3 is much better in the synthesis starting with 5. The 3-amino-2H-azirine 3 has been used as a building block of the dipeptide moieties Aib-Pro in the synthesis of nonapeptide 17, the C-terminal 6-14 segment of the peptaibole trichovirin I 1B. The structure of 17 was established by single-crystal X-ray crystallography.