172946-56-4

Upstream product

• 39716-58-0 pent-4-enoyl chloride 
• 591-80-0 pent-4-enoic acid 
• 23356-96-9 (S)-1-Pyrrolidin-2-yl-methanol 
• 63521-92-6 4-pentenoic anhydride 

Downstream Products

• 89597-97-7 (2S)-benzyloxymethyl-pyrrolidine 

Relevant academic research and scientific papers

The Pent-4-enoyl Group: A Novel Amine-Protecting Group That Is Readily Cleaved under Mild Conditions

Primary and secondary amines are readily protected as N-pent-4-enoyl derivatives, the resulting N-pent-4-enamides being usually highly crystalline.Deprotection is rapidly and efficiently effected under mild conditions by treatment with 3 equiv of iodine in aqueous THF solution.Although an oxidizing medium, these deprotection conditions do not affect oxidizable functionalities including p-methoxybenzyl ethers and alkyl sulfides.

Conformationally Restricted Peptide Mimetics: The Incorporation of 6,5-Bicyclic Lactam Ring Skeleton into Peptides

This manuscript describes a convenient procedure for the synthesis of peptide fragments containing 6,5-bicyclic lactam-based conformational constraints.The syntheses capitalize on an electrochemical oxidation to functionalize a substituted proline derivative, an N-acyliminium ion-initiated cyclization in order to form a transient seven-membered-ring lactam, and a rearragement reaction to form the desired six-membered-ring lactam.The bicyclic lactam products were converted into peptide building blocks and the stereochemistry of the building blocks assigned using two-dimensional NMR techniques.Once synthesized, the building blocks were readily incorporated into peptide fragments with the use of standard peptide synthesis techniques.The synthetic route employed was shown to be compatible with both aryl and branched amino acid side chains.