Protecting groups for carbohydrate synthesis

Details Protecting groups for carbohydrate synthesis Protecting groups for carbohydrate synthesis

2005-10-11

2005-10-11

Wilson, James O. (Department: 1623)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

C536S004100, C536S018500, C536S022100, C536S025300, C536S123130, C525S333600, C525S054200, C560S029000, C560S183000, C562S508000, C544S299000, C568S327000, C435S006120, C436S518000, C514S300000

Reexamination Certificate

active

06953850

ABSTRACT:
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; X1is hydrogen, —CH2O—, —CH2NH—, —CH3, —CH2N3or —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 X1is hydrogen, CH3or N3.

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