C - Chemistry – Metallurgy – 07 – H
Patent
C - Chemistry, Metallurgy
07
H
C07H 1/00 (2006.01) C07H 3/04 (2006.01) C07H 5/06 (2006.01) C07H 5/10 (2006.01) C07H 15/04 (2006.01) C07H 15/18 (2006.01) C07H 19/056 (2006.01)
Patent
CA 2724064
The present invention relates to novel synthesis routes for preparation of thiodigalactosides of the general formula (12). The method comprises the use of a 3-azido-galactosyl thiouronium salt derivative, which is activated to the corresponding thiol in situ, which in turn is directly reacted with a 3-azido-galactosyl bromide resulting in the 3,3'-di-azido-thio-di-galactoside before the thiol has a chance to reduce the azido 10 group. Hence, in situ formation of the 3-azido-galactosyl thiol from the thiouronium salt is essential in the synthesis procedure, because any other method that generate the thiol separately results in extensive unwanted azide reduction.
La présente invention concerne des voies de synthèse inédites permettant la préparation de thiodigalactosides de formule générale (12). Ce procédé comprend l'utilisation d'un dérivé d'un sel de 3-azido-galactosylthiouronium, qui est activé pour donner le thiol correspondant in situ, ce dernier étant, à son tour, immédiatement amené à réagir avec un bromure de 3-azido-galactosyle, avec pour résultat la formation de 3,3'-di-azido-thio-di-galactoside, avant que le thiol ne puisse réduire le groupe azido 10. Par suite, la formation in situ de 3-azido-galactosylthiol à partir du sel de thioruonium se révèle essentielle dans cette procédure de synthèse, car tous les autres procédés générant le thiol séparément entraînent une importante réduction de l'azide, réduction qui n'est absolument pas souhaitable.
Forskarpatent I. Syd Ab
Smart & Biggar
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