title: Synthesis of D-Desosamine and Analogs by Rapid Assembly of 3-Amino Sugars.
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.
authors.affiliation: Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138 (USA).
authors.forename: Ziyang
authors.initials: Z
authors.lastname: Zhang
authors.affiliation: Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138 (USA).
authors.forename: Takehiro
authors.initials: T
authors.lastname: Fukuzaki
authors.affiliation: Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138 (USA). myers@chemistry.harvard.edu.
authors.forename: Andrew G
authors.initials: AG
authors.lastname: Myers
mesh_terms: D000606:Amino Sugars / Q000138:chemical synthesis / Q000737:chemistry*; D018360:Crystallography, X-Ray; D066244:Proton Magnetic Resonance Spectroscopy
chemical_list: D000606:Amino Sugars; C110125:desosamine
keywords: 3-amino sugars; Henry reaction; desosamine; macrolide antibiotics; γ-nitro alcohols