181506-75-2

Upstream product

• 115961-49-4 [2-phenyl-1-[[(phenylmethoxy)carbonyl]amino]ethyl]phosphinic acid 
• 87438-94-6 ethyl 2-isobutylacrylate 
• 768-90-1 1-Adamantyl bromide 
• 181506-74-1 Ethyl 2-[[hydroxy[2-phenyl-1-[[(phenylmethoxy)carbonyl]amino]ethyl]phosphinyl]methyl]-4-methylpentanoate 

Downstream Products

• 1026214-10-7 2-[(Adamantan-1-yloxy)-(1-amino-2-phenyl-ethyl)-phosphinoylmethyl]-4-methyl-pentanoic acid 
• 182193-48-2 3-(Adamantan-1-yloxy)-2-benzyl-5-isobutyl-3-oxo-3λ⁵-[1,3]azaphosphinan-6-one 
• 181506-73-0 2-[(Adamantan-1-yloxy)-(1-benzyloxycarbonylamino-2-phenyl-ethyl)-phosphinoylmethyl]-4-methyl-pentanoic acid 
• 182193-49-3 2-[(Adamantan-1-yloxy)-(1-amino-2-phenyl-ethyl)-phosphinoylmethyl]-4-methyl-pentanoic acid ethyl ester 

Relevant academic research and scientific papers

Protection of the hydroxyphosphinyl function of phosphinic dipeptides by adamantyl. Application to the solid-phase synthesis of phosphinic peptides

To develop solid-phase synthesis of phosphinic peptides, different FmocXaaΦ{PO(OAd)CH2}XaaOH building blocks have been prepared, where Fmoc is (fluorenylmethoxy)carbonyl. In this respect, the protection of the hydroxyphosphinyl function in these phosphinic dipeptides by the adamantyl group turns out to be convenient. The phosphinic adamantyl esters are completely stable in basic conditions and can be removed under relatively mild acidic conditions. Using these building blocks, despite the bulkiness of the adamantyl group, no particular problem of coupling was observed during the solid-phase synthesis of phosphinic peptides by the Fmoc strategy. The developed methodology is of particular interest to facilitate the development of potent inhibitors of zinc-metalloproteases.