Building carbohydrates on the dioxanone scaffold: stereoselective synthesis of d-glycero-d-manno-2-octulose |
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| Authors: | Nagarjuna Palyam Izabella Niewczas Marek Majewski |
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| Institution: | aDepartment of Chemistry, University of Saskatchewan, 110 Science Place, Saskatoon, SK, Canada S7N 5C9 |
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| Abstract: | The title compound has been synthesized via two proline-catalyzed aldol addition reactions of 2,2-dialkyl-1,3-dioxan-5-ones: the first addition to 1,3-dithiane-2-carboxaldehyde, followed by reduction to the corresponding diol, protection of the OH groups and dithiane hydrolysis afforded a protected d-ribose that was used in the second aldol addition reaction. |
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| Keywords: | Higher sugars Organocatalysis Proline Stereoselective aldol reaction Dioxanone |
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