120060-98-2Relevant articles and documents
SIMULTANEOUS USE OF N-Fmoc AND OTmse PROTECTIVE GROUPS IN THE SYNTHESIS OF PEPTOLYTIC SENSITIVE PEPTIDES
Vanfleteren, L.,Anteunis, M. J. O.
, p. 505 - 518 (2007/10/02)
The combined use of Fmoc (fluorenylmethoxycarbonyl) as N-protection and Tmse (trimethylsilylethyl) as O-protection during demanding fragment condensation mediated by Bop-Cl (N,N'-bis(3-oxo-2-oxazolidinyl)phosphinyl chloride) has been explored in the preparation of useful synthons that are sensitive to acidic and even basic hydrolyses.Stepwise deprotection by morfoline (Fmoc-deprotection) followed by F--mediated removal of Tmse results in a very effective peptide synthesis strategy, as exemplified by the preparation of i.a.Phg-MePhe-Thz.Similarly, combinations of N-Boc, O-Tmse peptide esters are also possible that allow the preparation of +H2-MePhe-Thz-OTmse (via Boc-MePhe-Thz-OTmse) without competitive DKP formation.