title: syn additions to 4alpha-epoxypyranosides: synthesis of L-idopyranosides.
abstract: The syn-selective addition of organozinc compounds to 4alpha-epoxypyranosides (4alpha-EPs), generated from methyl beta-D-glucoside or aminoglucoside, provides an efficient route to pyranosides with alpha-L-ido configurations, including L-iduronic acid, neosamine B, and higher monosaccharide derivatives.
authors.affiliation: Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, IN 47907-2084, USA.
authors.forename: Gang
authors.initials: G
authors.lastname: Cheng
authors.forename: Renhua
authors.initials: R
authors.lastname: Fan
authors.forename: Jesús M
authors.initials: JM
authors.lastname: Hernández-Torres
authors.forename: Fabien P
authors.initials: FP
authors.lastname: Boulineau
authors.forename: Alexander
authors.initials: A
authors.lastname: Wei
mesh_terms: D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008745:Methylation; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D002241:Carbohydrates; D004852:Epoxy Compounds