title: Addition of lithiated C-nucleophiles to 2,3-O-isopropylidene-D-erythronolactone: stereoselective formation of a furanose C-disaccharide.
abstract: Addition of PhLi and lithiated dithianes to 2,3-O-isopropylidene-D-erythronolactone affords lactols, which are reduced with Et3SiH to the corresponding C-glycosides, the structures of two of which have been solved by X-ray diffraction. The use of a d-ribose-derived lithiated dithiane nucleophile in this chemistry allows for the convenient construction of a furanose C-disaccharide.
authors.affiliation: Department of Chemistry, Youngstown State University, 1 University Plaza, Youngstown, Ohio 44555-3663, USA.
authors.forename: Jason L
authors.initials: JL
authors.lastname: McCartney
authors.forename: Christopher T
authors.initials: CT
authors.lastname: Meta
authors.forename: Robert M
authors.initials: RM
authors.lastname: Cicchillo
authors.forename: Matthew D
authors.initials: MD
authors.lastname: Bernardina
authors.forename: Timothy R
authors.initials: TR
authors.lastname: Wagner
authors.forename: Peter
authors.initials: P
authors.lastname: Norris
mesh_terms: D002236:Carbohydrate Conformation; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry; D007783:Lactones / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry; D011807:Quinolizines / Q000737:chemistry; D012266:Ribose / Q000737:chemistry; D013237:Stereoisomerism; D013457:Sulfur Compounds / Q000737:chemistry; D014961:X-Ray Diffraction
chemical_list: D004187:Disaccharides; D006027:Glycosides; D007783:Lactones; D009942:Organometallic Compounds; D011807:Quinolizines; D013457:Sulfur Compounds; C438055:dithiane; D012266:Ribose; D008094:Lithium