Abstract

GONZALEZ, Denia; VINENT, Gemma; RODRIGUEZ, María del Carmen  and  RODRIGUEZ, Mercedes. Selectivity: design criterion for complex reactions. Vaccimonitor [online]. 2013, vol.22, n.3, pp.47-50. ISSN 1025-028X.

The gangliosides are glycosphingolipids that are distributed in the organism in different forms. The presence of the ganglioside N-Glycolil GM3 (NGcGM3) has been described in human tumoral cells, that is why it has became an attractive target for the specific antitumoral therapy. This molecule is the main component of the vaccine candidate for breast cancer in clinical trials phase. Lactose acceptor is a key intermediate to obtain this ganglioside by chemical synthesis, the protection of the positions 3´,4´ of lactose with an isopropiliden group is necessary in the synthesis of lactose acceptors that will be used to form part of oligosaccharides and glycoconjugates. This work is focused in the reaction to obtain 3',4'-lactose-isopropiliden, an intermediate in lactose acceptor synthesis. The reaction conditions were studied and the best results were found working at +1 level of temperature and -1 level of time reaction. The reaction was made in a 5 L reactor and the results were reproducible. The thin layer semi-quantitative chromatography was chosen to quantify the amount of the isomers 3´,4´ and 4',6'-lactose isopropiliden obtained in the reaction.

Keywords : multiple reactions; selectivity; 3'; 4'-lactose-isopropiliden.

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