Synthesis of new fucose-containing carbohydrate derivatives

作者: Markus Hederos , Gyula Dekany , Karoly Agoston , Elise Champion

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摘要: A method for the synthesis of a compound formula (1) or salt thereof, wherein is carbohydrate linker which lactosyl moiety consists and at least one monosaccharide unit selected from group consisting of: glucose, galactose, N -acetylglucosamine, fucose -acetyl neuraminic acid; R 1 following anomeric protecting groups: a) -OR 2 , removable by catalytic hydrogenolysis; b) -SR 3 an optionally substituted alkyl, aryl benzyl; c) -NH- C(R")=C(R') each R' independently electron withdrawing -CN, -COOH, -COO-alkyl, -CO-alkyl, -CONH -CONH- alkyl -CON(alkyl) two R'-groups are linked together form -CO-(CH ) 2-4 -CO- thus form, with carbon atom to they attached, 5-7 membered cycloalkan-1,3-dione, in dione any methylene groups groups, R" H fucosyl donor (2) X guanosine diphosphatyl moiety, lactose azide, fluoride, phenoxy-, pyridinyloxy-, 3-oxo-furanyloxy- (A), 1,3,5-triazinyloxy- (B), 4-methylumbelliferyloxy-group (C), (D) vicinal represent =C(R b group, c alkoxy, amino, alkylamino dialkylamino, d H, -C(=O)R e OH, alkylamino, hydrazino, alkylhydrazino, dialkylhydrazino trialkylhydrazino, reacted acceptor H-A-R as defined above, under catalysis enzyme capable transferring fucose. 1', its use manufacture human milk oligosaccharides, also provided.

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