Protecting groups for carbohydrate synthesis

Details Protecting groups for carbohydrate synthesis Protecting groups for carbohydrate synthesis

C - Chemistry, Metallurgy

07

H

C07H 23/00 (2006.01) C07H 1/00 (2006.01) C07H 5/00 (2006.01) C07H 5/04 (2006.01) C07H 5/10 (2006.01) C07H 7/04 (2006.01) C07H 7/06 (2006.01) C07H 9/04 (2006.01) C07H 15/02 (2006.01) C07H 15/207 (2006.01) C07H 15/26 (2006.01)

Patent

CA 2360069

The invention provides collections of orthogonally-protected monosaccharides as universal building blocks for the synthesis of glycoconjugates of non-carbohydrate molecules, neo-glycoconjugates and oligosaccharides. This orthogonal protection strategy allows for the specific deprotection of any substituent on the saccharide ring, and greatly facilitates targeted or library-focused carbohydrate-related syntheses. In particular, the invention provides a universal monosaccharide building block of General Formula (I) or General Formula (II) in which A is a leaving group; X is hydrogen, O, N or N3; X1 is hydrogen, - CH2O-, -CH2NH-, -CH3, -CH2N3 or -COO-; and B, C, D and E are protecting groups that can be cleaved orthogonally, and in which B, C, D and E are absent when X is hydrogen or N3, and E is absent when X1 is hydrogen, CH3 or N3.

L'invention concerne des collections de monosaccharides protégés orthogonalement, utilisés comme blocs de construction universels pour la synthèse de glycoconjugués de molécules non glucidiques, de néo-glycoconjugués et d'oligosaccharides. Cette stratégie de protection orthogonale permet la déprotection spécifique de n'importe quel substituant sur le cycle de saccharide, et facilite considérablement les synthèses relatives aux glucides ciblées ou focalisés sur des banques. En particulier, l'invention concerne un bloc de construction de monosaccharides universel de la formule générale (I) ou de la formule générale (II) dans lesquelles A représente un groupe partant; X représente hydrogène, O, N ou N3; X1 représente hydrogène -CH2O-, -CH2NH-, -CH3, -CH2N3 ou -COO-; et B, C, D et E sont des groupes protecteurs pouvant être clivés orthogonalement, et B, C, D et E sont absents lorsque X représente hydrogène ou N3 et E est absent lorsque X1 représente hydrogène, CH3 ou N3.

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