731807-68-4

Upstream product

• 389127-43-9 (R)-methyl 2-allylpyrrolidine-2-carboxylate 
• 112348-45-5 (R)-N-(tert-butoxycarbonyl)-2-allylproline methyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 144085-23-4 N-tert-butoxycarbonyl-L-α-allylproline 

Downstream Products

• 797760-58-8 (2R,5'R)-3-[4-(2,6-dichlorobenzyloxy)phenyl]-2-(1-tert-butoxycarbonyl-6-oxo-1,7-diazaspiro[4.4]nonane-7-yl)propanoic acid 
• 797760-57-7 (2S,5'R)-3-[4-(2,6-dichlorobenzyloxy)phenyl]-2-(1-tert-butoxycarbonyl-6-oxo-1,7-diazaspiro[4.4]nonane-7-yl)propanoic acid 
• 797760-55-5 (2S,5'R)-3-[4-(2,6-dichlorobenzyloxy)phenyl]-2-(1-tert-butoxycarbonyl-6-oxo-1,7-diazaspiro[4.4]nonane-7-yl)propanoic acid methyl ester 

Relevant academic research and scientific papers

Evaluation of lactam-bridged neurotensin analogues adjusting ψ(Pro 10) close to the experimentally derived bioactive conformation of NT(8-13)

The neurotensin C-terminal hexapeptide, NT(8-13), which has been found to adopt a β-strand-like conformation while bound to the NT1 receptor, was modified by the introduction of conformational constraints. Synthesis of the four stereoisomeric 4.4-spirolac

Improved synthesis of a [4.4]-spirolactam β-turn mimetic as surrogate of the didemnin side chain dipeptide Pro-N-Me-D-Leu

An efficient synthesis of [4.4]-spirolactam restricted derivatives of the didemnin side chain dipeptide L-Pro-N-Me-D-Leu is described. This methodology involves: (a) peptide coupling of N-Boc-2-allylproline with D-Leu-OBn; (b) OsO4/NaIO4 mediated allyl oxidation and intramolecular cyclization to the corresponding cyclic hemiaminals; and (c) NaBH4 mediated reduction of an intermediate N-acyliminium ion. This synthetic strategy gave significant better results than the previously reported strategies for the synthesis of [4.4]-spirolactam β-turn mimetics.