title: Two-step synthesis of per-O-acetylfuranoses: optimization and rationalization.
abstract: A simple two-step procedure yielding peracetylated furanoses directly from free aldoses was implemented. Key steps of the method are (i) highly selective formation of per-O-(tert-butyldimethylsilyl)furanoses and (ii) their clean conversion into acetyl ones without isomerization. This approach was easily applied to galactose and structurally related carbohydrates such as arabinose, fucose, methyl galacturonate and N-acetylgalactosamine to give the corresponding peracetylated targets. The success of this procedure relied on the control of at least three parameters: (i) the tautomeric equilibrium of the starting unprotected oses, (ii) the steric hindrance of both targeted furanoses and silylating agent, and finally, (iii) the reactivity of each soft nucleophile during the protecting group interconversion.
authors.affiliation: Ecole Nationale Supérieure de Chimie de Rennes, CNRS, UMR 6226, Avenue du Général Leclerc, CS 50837, 35708 Rennes Cedex 7, France.
authors.forename: Rémy
authors.initials: R
authors.lastname: Dureau
authors.forename: Laurent
authors.initials: L
authors.lastname: Legentil
authors.forename: Richard
authors.initials: R
authors.lastname: Daniellou
authors.forename: Vincent
authors.initials: V
authors.lastname: Ferrières
mesh_terms: D000107:Acetylation; D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D004987:Ethers; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry
chemical_list: D004987:Ethers; D009005:Monosaccharides; D012821:Silanes