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 ono 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.
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