Synthesis of trisaccharide 6'SiaLeC and its 6-O-Su derivative.
Mendeleev Communs., 22 (4), pp. 194 - 195, (2012)
M. M. Shemyakin−Yu. A. Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 117997 Moscow, Russian Federation
The synthetic approach to 6'SiaLec and its 6-O-Suderivative comprised α-sialylation of a protected Lecderivative, 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).