title: Synthesis of 3-C-(6-O-acetyl-2,3,4-tri-O-benzyl-alpha-D-mannopyranosyl)-1-propene: a caveat.
abstract: During the preparation of 3-C-(6-O-acetyl-2,3,4-tri-O-benzyl-alpha-D-mannopyranosyl)-1-propene, using a published Sakurai-type reaction on the parent methyl glycoside, some observations were made on the sensitivity to reaction conditions that were not previously reported. This Note presents the study of this allylation reaction followed by acetolysis, which ultimately led to the best conditions to obtain the C-glycoside, and on further transformations to yield the corresponding aldehydic and acidic derivatives.
authors.affiliation: Laboratoire de Chimie Bioorganique et de Biotechnologie Moléculaire et Cellulaire, UMR 7001 CNRS, Ecole Nationale Supérieure de Chimie de Paris, F-75005, Paris, France. cgirard@ext.jussieu.fr
authors.forename: Christian
authors.initials: C
authors.lastname: Girard
authors.forename: Marie-Laure
authors.initials: ML
authors.lastname: Miramon
authors.forename: Tanguy
authors.initials: T
authors.lastname: de Solminihac
authors.forename: Jean
authors.initials: J
authors.lastname: Herscovici
mesh_terms: D000107:Acetylation; D000498:Allyl Compounds / Q000737:chemistry*; D001593:Benzyl Compounds / Q000737:chemistry*; D008362:Mannosides / Q000737:chemistry*; D009005:Monosaccharides / Q000138:chemical synthesis*; D009993:Osmium Tetroxide / Q000737:chemistry; D010084:Oxidation-Reduction; D010504:Periodic Acid / Q000737:chemistry; D014297:Trimethylsilyl Compounds / Q000737:chemistry
chemical_list: C472677:3-C-(6-O-acetyl-2,3,4-tri-O-benzyl-mannopyranosyl)-1-propene; D000498:Allyl Compounds; D001593:Benzyl Compounds; D008362:Mannosides; D009005:Monosaccharides; D014297:Trimethylsilyl Compounds; D010504:Periodic Acid; C009288:metaperiodate; D009993:Osmium Tetroxide