Synthesis of locked nucleic acid derivatives

C - Chemistry – Metallurgy – 07 – H

Patent

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C07H 19/16 (2006.01) C07H 19/04 (2006.01) C07H 19/06 (2006.01) C07H 21/00 (2006.01)

Patent

CA 2484526

The invention relates to a novel strategy for the synthesis of Locked Nucleic Acid derivatives, such as .alpha.-L-oxy-LNA, amino-LNA, .alpha.-L-amino-LNA, thio-LNA, .alpha.-L-thio-LNA, seleno-LNA and methylene LNA, which provides scalable high yielding reactions utilising intermediates that also can produce other LNA analogues such as oxy-LNA. Also, the compounds of the formula X are important intermediates that may be reacted with varieties of nucleophiles leading to a wide variety of LNA analogues. (Formula I)

L'invention concerne une nouvelle stratégie permettant la synthèse de dérivés de LNA (Locked Nucleic Acid) tels que .alpha.-L-oxy-LNA, amino-LNA, .alpha.-L-amino-LNA, thio-LNA, .alpha.-L-thio-LNA, séléno-LNA et méthylène LNA. Cette stratégie permet la mise en oeuvre de réactions à haut rendement, modulables, comprenant l'utilisation d'intermédiaires qui permettent également d'obtenir d'autres analogues de LNA tels que les oxy-LNA. L'invention concerne également les composés représentés par la formule X, qui sont des intermédiaires importants capables de réagir avec divers nucléophiles et permettant ainsi d'obtenir une large variété d'analogues de LNA. (formule X)

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