title: Glycosylation of 'basic' alcohols: methyl 6-(hydroxymethyl)picolinate as a case study.
abstract: Glycosylation is promoted by acid promoters rendering the reactions with basic acceptors challenging. This report presents an in depth study involving methyl 6-(hydroxymethyl)picolinate as the model acceptor and 22 glycosyl donors to afford the desired glycosides in good yields ranging from 46% to 85%. Several parameters were evaluated, including the protecting groups of the glycosyl donor, the leaving group at the anomeric center, and the promoter. The influence of the pyridine ring was evident with a benzene-based acceptor affording high yields of glycoside (79%) in comparison to the pyridine-based acceptor (46%). The present work provides a general and reliable access to pyridine-containing glycosides.
authors.affiliation: Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, Laboratoire de Chimie Organique 2 - Glycochimie, UMR 5246, CNRS, Université Claude Bernard Lyon 1, 43 Boulevard du 11 Novembre 1918, F-69622 Villeurbanne, France.
authors.forename: Shuai
authors.initials: S
authors.lastname: Wang
authors.forename: Dominique
authors.initials: D
authors.lastname: Lafont
authors.forename: Jani
authors.initials: J
authors.lastname: Rahkila
authors.forename: Benjamin
authors.initials: B
authors.lastname: Picod
authors.forename: Reko
authors.initials: R
authors.lastname: Leino
authors.forename: Sébastien
authors.initials: S
authors.lastname: Vidal
mesh_terms: D000117:Acetylglucosamine / Q000737:chemistry; D000438:Alcohols / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D005643:Fucose / Q000737:chemistry; D005690:Galactose / Q000737:chemistry; D005947:Glucose / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis*; D006031:Glycosylation; D007785:Lactose / Q000737:chemistry; D008358:Mannose / Q000737:chemistry; D010848:Picolinic Acids / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*; D012210:Rhamnose / Q000737:chemistry
chemical_list: D000438:Alcohols; D006027:Glycosides; D010848:Picolinic Acids; D011725:Pyridines; D005643:Fucose; D005947:Glucose; D007785:Lactose; C023666:pyridine; D008358:Mannose; D012210:Rhamnose; D000117:Acetylglucosamine; D005690:Galactose