New and general synthesis of beta-C-glycosylformaldehydes from easily available beta-C-glycosylpropanones.
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.
Norsikian
Stéphanie
S
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
Zeitouni
Jennifer
J
Rat
Stéphanie
S
Gérard
Sylvie
S
Lubineau
André
A
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
D000096:Acetone; D005557:Formaldehyde; D005947:Glucose; D007785:Lactose; D000117:Acetylglucosamine; D005690:Galactose