100496-19-3Relevant articles and documents
Synthesis of terminal disaccharide of Forssman's antigen and some of its analogs as spacered glycosides and free disaccharides
Ovchinnikova,Ter-Grigoryan,Pazynina,Bovin
, p. 55 - 68 (2007/10/03)
Spacered terminal disaccharide of Forssman's antigen GalNAcα1-3GalNAcβ1-Osp, its analog GalNAcα1-3GalNAcα1-Osp, and disaccharides Galβ1-3GalNAcβ1-Osp and Galα1-3GalNAcα1-Osp [where sp denotes the (CH2)3NHCOCF3 spacer] were synthesized. Spacered disaccharides were obtained from the (3-trifluoroacetamidopropyl)-2-acetamido-4,6-O-benzylidene-2-deoxy-β-D- galactopyranoside and its α-and β-analogs in which the 2-azido group was substituted for the 2-acetamido group. The azide glycosyl acceptors gave higher yields of the disaccharides. Azide glycosyl acceptors were prepared by the stereoselective glycosylation of 3-trifluoroacetamidopropanol with a mixture of 1-O-acetates of the 2-azido-3,4,6-tri-O-acetyl-2-deoxy-D-galactopyranose anomers in the presence of Lewis acids. Disaccharides Galα1-3GalNAc and GalNAcα1-3GalNAc were obtained from the benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside.