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• W2053621436 abstract "A practical access to glucose-based and allose-based spirooxazolidinones is reported. The synthetic sequence consisting of TEMPO-catalyzed oxidation of 1,2:5,6-di-O-isopropylidene-α-d-glucofuranose, Henry reaction, and reduction provides amino alcohol with allo-configuration on a multigram scale. Alternatively, water elimination from Henry products followed by a rehydration gives an access to diastereomerically pure glucose-based nitro alcohol which upon reduction provides complementary amino alcohol with gluco-configuration. The latter amino alcohols are transformed into spirooxazolidinones (3-spiropseudonucleosides) via their N-Cbz or N-phenylcarbamate derivatives. The title compounds easily undergo N-derivatization and give highly crystalline materials. Two of the newly obtained (5+5) 3-spiropseudonucleosides are characterized by X-ray crystallography." @default.
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• W2053621436 date "2013-06-01" @default.
• W2053621436 modified "2023-10-11" @default.
• W2053621436 title "A practical access to glucose- and allose-based (5+5) 3-spiropseudonucleosides from a common intermediate" @default.
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• W2053621436 doi "https://doi.org/10.1016/j.carres.2013.04.008" @default.
• W2053621436 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/23665157" @default.
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