Synthesis of 4-alkoxy-n-acetylneuraminic acid

Details Synthesis of 4-alkoxy-n-acetylneuraminic acid Synthesis of 4-alkoxy-n-acetylneuraminic acid

C - Chemistry, Metallurgy

07

H

C07H 15/04 (2006.01)

Patent

CA 2195872

This invention relates to an improved process for the synthesis of 4-alkoxy-N- acetylneuraminic acids. According to the process of the invention, N- acetylneuraminic acid is first alkylated at C-1 and C-2, and then the vicinal hydroxyl groups at C-8 and C-9 are protected through the formation of a ketal. The resulting protected alkyl ester alkyl ketoside is then alkylated at the C- 4 position whereby the hydrogen of the C-4 hydroxyl group is replaced with an alkyl group to form an alkoxy group. Deprotection is accomplished through the removal of the ketal group at C-8 and C-9 and removal of the alkyl groups at C- 1 and C-2, thereby producing the 4-alkoxy-N-acetylneuraminic acid.

Cette invention se rapporte à un procédé de synthèse amélioré des acides 4-alcoxy-acétylneuraminiques. Selon le procédé de l'invention, l'acide N-acétylneuraminique est d'abord alkylé aux positions C-1 et C-2, puis les groupes hydroxyle voisins aux positions C-8 et C-9 sont protégés par la formation d'un cétal. L'alkyle ester alkyle cétoside protégé obtenu est ensuite alkylé à la position C-4, l'hydrogène du groupe hydroxyle en C-4 étant remplacé par un groupe alkyle pour former un groupe alcoxy. La déprotection s'effectue par le retrait du groupe cétal aux positions C-8 et C-9 et le retrait des groupes alkyle aux positions C-1 et C-2, ce qui permet d'obtenir l'acide 4-alcoxy-N-acétylneuraminique.

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