A Novel Strategy for the Synthesis of Ammonium 3-Deoxy-D-manno-2-octulosonate (Ammonium KDO) from Lower Monosaccharides. C-C Bond Construction at C6 of D-Mannose via Cobaloxime-Mediated Radical Alkyl-Alkenyl Cross Coupling
Our synthesis of ammonium 3-deoxy-D-manno-2-octulosonate (ammonium KDO, 16) from D-mannose (3) proceeds in 10 one-flask operations in 1.5-1.6percent overall yield (66percent per operation).The strategic reaction is a C-C bond construction at C6 of D-mannose via photochemically induced radical cross coupling of α-ethoxyacrylonitrile with an alkyl cobaloxime derivative of D-mannose, in aqueous ethanol without protection of carbohydrate hydroxyls.In this paper we provide full experimental details of our KDO synthesis.In addition we provide some observations and insights on vanadium-catalyzed oxidations of α-hydroxy acids to α-keto acids.
Branchaud, Bruce P.,Meier, Mark S.
p. 1320 - 1326
(2007/10/02)
A SYNTHESIS OF AMMONIUM 3-DEOXY-D-MANNO-2-OCTULOSONATE (AMMONIUM KDO) FROM D-MANNOSE VIA COBALOXIME-MEDIATED RADICAL ALKYL-ALKENYL CROSS COUPLING
We report a synthesis of the ammonium salt of the 8-carbon monosaccharide 3-deoxy-D-manno-2-octulosonic acid (KDO) starting from D-mannose.The key C-C bond construction in our synthetic strategy is a novel alkyl cobaloxim mediated radical alkyl-alkenyl cr
Branchaud, Bruce P.,Meier, Mark S.
p. 3191 - 3194
(2007/10/02)
Structural Analogs of 2-Keto-3-deoxy-D-mannooctulosonic Acid
The synthesis of 3-deoxy sugars (4-8) has been carried out as structural analogs of 2-keto-3-deoxy-D-mannooctulosonic acid (KDO; 1).
Sengupta, Dibyendu,Cherniak, Robert
p. 85 - 87
(2007/10/02)
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