HYDRAZINOLYSIS OF DDE - COMPLETE ORTHOGONALITY WITH ALOC PROTECTING GROUPS

Authors
ROHWEDDER B MUTTI Y DUMY P MUTTER M
Citation
B. Rohwedder et al., HYDRAZINOLYSIS OF DDE - COMPLETE ORTHOGONALITY WITH ALOC PROTECTING GROUPS, Tetrahedron letters, 39(10), 1998, pp. 1175-1178
Citations number
11
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
10
Year of publication
1998
Pages
1175 - 1178
Database
ISI
SICI code
0040-4039(1998)39:10<1175:HOD-CO>2.0.ZU;2-W
Abstract
Hydrazinolysis of Dde group is troublesome in the presence of Aloc pro tected peptides. We elucidate that reduction of the Aloc double bond o ccurs both in solution and on solid support preventing the subsequent Aloc deprotection and resulting in mixtures difficult to purify. We re port here that addition of allyl alcohol as scavenger circumvents this side reaction and provides a complete orthogonality between Dde and A loc in solution and solid phase peptide synthesis. (C) 1998 Elsevier S cience Ltd. All rights reserved.