Modulation of the relative reactivities of carbohydrate secondary hydroxyl groups. Modification of the hydrogen bond network |
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Authors: | Nicolas Moitessier Yves Chapleur |
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Institution: | Groupe SUCRES, Unité Mixte 7565 CNRS, Université Henri Poincaré-Nancy 1, B.P. 239, F-54506 Nancy-Vandoeuvre, France |
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Abstract: | An approach towards the control of the relative regioselectivity of the secondary hydroxyl groups is presented. Original protecting groups, which are capable of specific intramolecular hydrogen bonds and are likely to modulate the partial charges of the oxygen atoms, have been developed. Qualitative NMR experiments confirmed the existence of the expected hydrogen bonds and shed light on the perturbation of the cooperative intramolecular hydrogen bond network. Further reactivity studies are presented and confirm the potential of protecting group-mediated regioselective functionalization of carbohydrates. |
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