Search

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. [ABSTRACT FROM AUTHOR]

Key step in the synthesis of D-desosamine and analogs (V) is the chromatography-free procedure for the coupling of chiral nitrobutanols (I) with glyoxal to give pure 3-nitro sugars by crystallization. [ABSTRACT FROM AUTHOR]