351356-12-2

Upstream product

• 79-30-1 isobutyryl chloride 
• 66831-17-2 (2S,4R)-methyl 4-(benzyloxy)pyrrolidine-2-carboxylate hydrochloride 

Downstream Products

• 351356-45-1 methyl N-[(tert-butoxy)carbonyl]-(S)-alanyl-dimethylglycyl-(2S,4R)-4-(benzyloxy)prolyl-(S)-valinate 
• 351356-50-8 Boc-Ala-Aib-Hyp(Bn)-OH 
• 351356-04-2 methyl N-[(tert-butoxy)carbonyl]-(S)-alanyl-dimethylglycyl-(2S,4R)-4-(benzyloxy)prolinate 
• 351356-27-9 methyl (2S,4R)-4-(benzyloxy)-N-(2,2-dimethyl-2H-azirin-3-yl)prolinate 
• 351356-17-7 methyl (2S,4R)-4-(benzyloxy)-N-(2-methyl-1-thioxopropyl)prolinate 

Relevant academic research and scientific papers

A novel 2H-azirin-3-amine as a dipeptide (Aib-Hyp) synthon

The synthesis of methyl (2S,4R)-4-(benzyloxy)-N-(2,2-dimethyl-2H-azirin-3-yl)prolinate (10), a novel 2H-azirin-3-amine ('3-amino-2H-azirine'), is described (Scheme 1). The reaction of methyl (2S,4R)-N-(2methylpropanoyl)-4-(benzyloxy)prolinate (7) with Lawesson reagent gave methyl (2S,4R)-4-(benzyloxy)-N-[2-(methylthio)propanoyl]prolinate (8) and consecutive treatment with COCl2, 1,4-diazabicyclo[2.2.2]octane (DABCO), and NaN3 led to 10. The use of 10 as a building block of the dipeptide Aib-Hyp (Aib=2-aminoisobutyric acid, Hyp=(2S,4R)-4-hydroxyproline) is demonstrated by the syntheses of several model peptides (Scheme 2 and Table). The benzyl protecting group of the 4-OH function in Hyp in the model peptides has been removed in good yields.