Synthesis 1992; 1992(1/2): 46-48
DOI: 10.1055/s-1992-34178
short paper
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A New Synthesis of Ammonium 3-Deoxy-D-manno-octulosonate (Ammonium KDO) from D-Lyxose

B. Giese* , T. Linker
  • *Institut für Organische Chemie der Universität Basel, St. Johanns-Ring 19, CH-4056 Basel, Switzerland
Further Information

Publication History

Publication Date:
18 September 2002 (online)

The ammonium salt of 3-deoxy-D-manno-2-octulosonic acid (10) is synthesized from D-lyxose (2) via 1,2,3,4-tetra-O-acetyl-5-bromo-α-D-lyxopyranose (3) and radical C,C-bond formation with tert-butyl 2-(tributylstannylmethyl) propenoate (6). After deprotection and reduction, ozonolysis of 2,3-dideoxy-2-methylene -D-manno-octonic acid (9) yields the target molecule 10.