C(2)-(alfa-Mannosyl)indole: The Pivotal Intermediate Towards the Natural C-Glycopeptides

• Autorzy: Hassan, H.H.A.M. , Spies, H. S. , Bredenkamp, M. W.
• Języki publikacji: EN

Abstrakty

EN

Two different approaches were investigated to prepare the unusual modified peptide C(2)-mannosylated indole residue. Direct glycosylation of 2-metallated indoles or 2-trimethylsilylindole derivative by reaction with perbenzylated -D-mannopyranosyl bromide was incompatible due to the intermediate generation of a nucleophilic anomeric carbon atom followed by elimination of the functional group at C-2. Palladium-catalyzed coupling/cyclization approach was examined as a novel route towards indole-(C)- glycosides. Coupling of the mannopyranosyl donors with o-ethynylaniline derivative in the presence of Pd(0) followed by cyclization of the newly formed alditols were also described.

• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2000
• Tom: Vol. 74, nr 11
• Strony: 15889-1598
• Opis fizyczny: Bibliogr. 23 poz., rys.

Twórcy

autor

Hassan, H.H.A.M.

autor

Spies, H. S.

autor

Bredenkamp, M. W.

• Chemistry Department, Faculty of Science, Alexandria University, P.O. 425-Ibrahimia, 21321-Alexandria, Egypt,