title: New and general synthesis of beta-C-glycosylformaldehydes from easily available beta-C-glycosylpropanones.
abstract: A highly effective method for the introduction of a formyl group at the anomeric position of pyranosides was developed via enolisation of beta-C-D-glycopyranosylpropan-2-one using thermodynamic conditions then oxidative cleavage of the more substituted double bond. This sequence affords the desired aldehydes that are conveniently protected as aminals for purification and storage and easily regenerated using Dowex resin H+. In this paper, the syntheses of nine differently protected aldehydes derived from d-glucose, d-galactose, lactose and N-acetyl-d-glucosamine are presented. Our strategy proved to be very efficient in most cases excepted in the D-mannose series.
authors: Laboratoire de Chimie Organique Multifonctionnelle, UMR CNRS-UPS 8614 Glycochimie Moléculaire, Bât. 420, Université Paris Sud, F-91405 Orsay, France. stephanie.norsikian@icsn.cnrs-gif.fr
authors: Stéphanie
authors: S
authors: Norsikian
authors: Jennifer
authors: J
authors: Zeitouni
authors: Stéphanie
authors: S
authors: Rat
authors: Sylvie
authors: S
authors: Gérard
authors: André
authors: A
authors: Lubineau
mesh_terms: D000096:Acetone / Q000031:analogs & derivatives*; D000117:Acetylglucosamine / Q000737:chemistry; D005557:Formaldehyde / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D005690:Galactose / Q000737:chemistry; D005947:Glucose / Q000031:analogs & derivatives* / Q000737:chemistry*; D007785:Lactose / Q000737:chemistry; D010084:Oxidation-Reduction; D013816:Thermodynamics
chemical_list: D000096:Acetone; D005557:Formaldehyde; D005947:Glucose; D007785:Lactose; D000117:Acetylglucosamine; D005690:Galactose