916596-72-0Relevant academic research and scientific papers
Synthesis of a GM3 ganglioside analogue carrying a phytoceramide moiety by intramolecular glycosylation as a key step
Fujikawa, Kohki,Imamura, Akihiro,Ishida, Hideharu,Kiso, Makoto
experimental part, p. 2729 - 2734 (2009/04/11)
A novel analogue of ganglioside GM3, in which sphingosine was replaced with a phytosphingosine moiety, was synthesized by intramolecular glycosylation as a key step. Glucose, a reducing terminal of the saccharide, and phytoceramide were first tethered by succinic acid and the derivative used for the subsequent glycosidic bond formation. The obtained glycosyl phytoceramide was further glycosylated with the sialyl galactose residue to afford a fully protected GM3 derivative, which was converted into the desired, final compound by using conventional deprotection procedures.
A novel synthetic route to α-galactosyl ceramides and iGb3 using DTBS-directed α-selective galactosylation
Kimura, Akiyoshi,Imamura, Akihiro,Ando, Hiromune,Ishida, Hideharu,Kiso, Makoto
, p. 2379 - 2382 (2008/02/09)
A novel synthetic route to α-galactosyl ceramides and isoglobotrihexosylceramide (iGb3), which can activate NKT cells, was developed by exploiting a di-tert-butylsilylene-directed α-selective galactosylation procedure. Georg Thieme Verlag Stuttgart.
