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Synthesis of D ‐Desosamine and Analogs by Rapid Assembly of 3‐Amino Sugars
Author(s) -
Zhang Ziyang,
Fukuzaki Takehiro,
Myers Andrew G.
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201507357
Subject(s) - glyoxal , chemistry , nitro , ketone , stereochemistry , organic chemistry , combinatorial chemistry , alkyl
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.