502435-24-7Relevant articles and documents
Synthesis of β-D-Galp-(1→3)-β-D-Galp-(1→6)-[β-D-Galf- (1→4)]-D-GlcNAc, a tetrasaccharide component of mucins of Trypanosoma cruzi
Gallo-Rodriguez, Carola,Gil-Libarona, M.Agustina,Mendoza, Verónica M,De Lederkremer, Rosa M
, p. 9373 - 9380 (2007/10/03)
The synthesis of free β-D-Galp-(1→3)-β-D-Galp-(1→6)-[β-D-Galf- (1→4)]-D-GlcNAc and the corresponding alditol which has been previously isolated by reductive β-elimination of Trypanosoma cruzi glycoproteins are described. A convergent route was envisioned by condensing an acceptor derivative of β-D-Galf-(1→4)-D-GlcNAc with a donor derivative of β-D-Galp-(1→3)-D-Galp. The trichloroacetimidate method, as well as SnCl4-promoted condensation were utilized for the introduction of the galactofuranosyl unit. On the other hand, the glycosyl-aldonolactone approach, followed by reduction of the lactone with diisoamylborane, and further isomerization to the galactopyranose configuration gave the donor derivative, which was condensed by the trichloroacetimidate method. Moreover, a synthon for the introduction of the β-D-Galp-(1→3)-D-Galf unit is described.