In situ preparation of nucleoside phosphoramidites and their...

C - Chemistry – Metallurgy – 07 – F

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C07F 9/48 (2006.01) C07F 9/572 (2006.01) C07F 9/6533 (2006.01) C07F 9/6558 (2006.01) C07H 19/10 (2006.01) C07H 19/20 (2006.01) C07H 21/00 (2006.01)

Patent

CA 2226111

The invention provides novel bifunctional phosphitylating reagents and their application in in situ preparation of 5'-protected nucleoside phosphoramidites and synthesis of oligonucleotides. Bifunctional phosphitylating reagents according to the invention react quickly with nucleosides under weakly acidic conditions. In addition, the bifunctional phosphitylating reagents according to the invention generate chemoselectively the corresponding nucleoside phosphoramidites in situ, without need to purify the nucleoside phosphoramidites before using them in oligonucleotide synthesis. Finally, the bifunctional phosphitylating reagents according to the invention are relatively stable and easy to handle.

Nouveaux réactifs phosphitylisants bifonctionnels et leur application dans le préparation in situ de phosphoramidites de nucléosides protégés en 5' et la synthèse d'oligonucléotides. Ces réactifs bifonctionnels phosphitylisants réagissent rapidement avec les nucléosides dans des conditions faiblement acides. En outre ces mêmes réactifs génèrent de manière chimiosélective les phosphoramidites des nucléosides correspondant in situ, sans qu'il soit nécessaire de purifier les phosphoramidites de nucléosides avant de les utiliser pour la synthèse d'oligonucléotides. Enfin ces réactifs phosphitylisants sont relativement stables et faciles à manier.

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