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  • Title: Synthesis of D-Desosamine and Analogs by Rapid Assembly of 3-Amino Sugars.
    Author: Zhang Z, Fukuzaki T, Myers AG.
    Journal: Angew Chem Int Ed Engl; 2016 Jan 11; 55(2):523-7. PubMed ID: 26612347.
    Abstract:
    D-Desosamine is synthesized in 4 steps from methyl vinyl ketone and sodium nitrite. The key step in this chromatography-free synthesis is the coupling of (R)-4-nitro-2-butanol and glyoxal (trimeric form) mediated by cesium carbonate, which affords in crystalline form 3-nitro-3,4,6-trideoxy-α-D-glucose, a nitro sugar stereochemically homologous to D-desosamine. This strategy has enabled the syntheses of an array of analogous 3-nitro sugars. In each case the 3-nitro sugars are obtained in pure form by crystallization.
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