title: Practical synthesis of 2-keto-3-deoxy-D-glycero-D-galactononulosonic acid (KDN).
abstract: Reaction of propargylmagnesium bromide with 2,3;5,6-di-O-isopropylidene-D-mannonolactone followed by highly stereoselective reduction of the so-formed lactol with sodium borohydride gives a syn-diol from which practical syntheses of 2-keto-3-deoxy-D-glycero-D-galactononulosonic acid (KDN) and various partially protected derivatives have been achieved all of which feature the oxidative unmasking of the α-keto acid moiety from the alkyne.
authors: Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, USA. DCrich@chem.wayne.edu
authors: David
authors: D
authors: Crich
authors: Chandrasekhar
authors: C
authors: Navuluri
mesh_terms: D002384:Catalysis; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013400:Sugar Acids / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D013400:Sugar Acids; C050008:3-deoxyglycero-galacto-nonulosonic acid