Programmable one-pot oligosaccharide synthesis

In an effort to develop a broadly applicable approach to the facile one-pot synthesis of oligosaccharides, the reactivity of a number of p-methylpheny l thioglycoside (STol) donors which are either fully protected or have one hydroxyl group exposed has been quantitatively determined by HPLC. We have characterized and quantified the influence on reactivity of the structural effects of different monosaccharide cores and different protecting groups o n each glycoside donor. In addition, we have established a correlation betw een glycosyl donor reactivity and the chemical shift of the anomeric proton by H-1 NMR. Using the reactivity data, we have created a database of thiog lycosides as glycosyl donors and demonstrated its utility in the easy and r apid one-pot assembly of various linear and branched oligosaccharide struct ures. In addition, we have developed the first computer program, OptiMer, f or use as a database search tool and guide for the selection of building bl ocks for the one-pot assembly of a desired oligosaccharide or a library of individual oligosaccharides.