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note
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All possible conformations of compounds 15 and 17 and their corresponding β-(1→4)-linked counterparts were generated by a Monte-Carlo conformation search (1000 steps) and energy-minimized with the AMBER force field. 9, 3, 9, and 9 conformers were found for compounds 15, its β-anomer, 17 and its β-anomer, respectively, within 3 kcal/mol of the global minima. Compound 15 was calculated to be 12.8 kcal/mol more stable than its β-anomer and compound 17 was calculated to be 7.0 kcal/mol more stable than its β-anomer. Similarly, the α-(1→4)-linked 2,3-di-O-acetylated disaccharide related to 15 was calculated to be 4.5 kcal/mol more stable than the corresponding β-(1→4)-linked saccharide, whereas in the case of the 2,6-di-O-acetylated disaccharide related to 17, the β-(1→4)-linked isomer was found to be 7 kcal/mol more stable. Thus, in the case of conversion 14→17 a significant influence of the tether on the diastereoselectivity was found.
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