104669-70-7Relevant academic research and scientific papers
New polymer-supported allyloxycarbonyl (Alloc) and propargyloxycarbonyl (Proc) amino-protecting reagents
Chinchilla, Rafael,Dodsworth, David J.,Nájera, Carmen,Soriano, José M.
, p. 809 - 812 (2003)
New polymer-supported reagents, Alloc-P-OSu and Proc-P-OSu, have been prepared from a polymeric N-hydroxysuccinimide (P-HOSu), and used as solid-supported reagents for the allyloxycarbonyl (Alloc) and propargyloxycarbonyl (Proc) protection of the amino group. These new polymeric reagents are safe and stable, the residual P-HOSu generated after the protection reaction can be easily separated by simple filtration and reused.
Selective Cleavage of the Allyl and Allyloxycarbonyl Groups through Palladium-Catalyzed Hydrostannolysis with Tributyltin Hydride. Application to the Selective Protection-Deprotection of Amino Acid Derivatives and in Peptide Synthesis
Dangles, O.,Guibe, F.,Balavoine, G.,Lavielle, S.,Marquet, A.
, p. 4984 - 4993 (1987)
N-Allyloxycarbonyl (Alloc) derivatives of amines and amino acids are quantitatively and very rapidly converted to free amino compounds by palladium-catalyzed hydrostannolytic cleavage with tributyltin hydride in the presence of a proton donor (acetic acid, p-nitrophenol, pyridinium acetate, water).A similar procedure can be used for the deprotection of allyl (All) carboxylates and allyl aryl ethers.Deprotection experiments were performed on various mixed N-Alloc and O-Bzl, N-Z and O-All, N-Alloc and O-t-Bu, and N-alloc- and N-Boc-protected amino acid derivatives.The palladium-catalyzed hydrostannolytic cleavage is fully compatible with the Bzl and Z protecting groups; furthermore the BOC and t-Bu groups and the Alloc and All groups appear to be ortogonal.The reliability of the Alloc methodology for temporary protection of the α-amino functions is ilustrated by the solid-phase synthesis of the biologically active undecapeptide substance P.
