G. V. Pazynina, I. S. Popova, I. M. Belyanchikov, A. B. Tuzikov, N. V. Bovin, “Synthesis of trisaccharide 6’ SiaLec and its 6-O-Su derivative”, Mendeleev Commun., 2012, Volume 22, Issue 4,Pages 194

This article is cited in 3 papers

Synthesis of trisaccharide 6’ SiaLe^c and its 6-O-Su derivative

G. V. Pazynina, I. S. Popova, I. M. Belyanchikov, A. B. Tuzikov, N. V. Bovin

M.M. Shemyakin–Yu.A. Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation

Abstract: The synthetic approach to 6'SiaLe^c and its 6-O-Su derivative comprised α-sialylation of a protected Le^c derivative, 2,3-di-OAcGalβ1-3(3-OAc-6-OBn)GlcNAcβ1-Osp (68% yield) as the key stage. Deprotection of the obtained trisaccharide (three stages, 79% overall yield) led to Neu5Acα2-6Galβ1-3GlcNAcβ1-Osp; partial deprotection followed by selective sulfation and total deprotection – to Neu5Acα2-6Galβ1-3(6-O-Su)GlcNAcβ1-Osp (four stages, 72% overall yield).

Keywords: Lewis C trisaccharide, sulfation, sialylation.

Language: English

DOI: 10.1016/j.mencom.2012.06.007