title: The Use of Pyranoside-into-Furanoside Rearrangement and Controlled O(5) → O(6) Benzoyl Migration as the Basis of a Synthetic Strategy To Assemble (1→5)- and (1→6)-Linked Galactofuranosyl Chains.
abstract: A new pyranoside-into-furanoside (PIF) rearrangement of selectively protected galactopyranosides, followed by controlled O(5) → O(6) benzoate migration, gives either 5-OH or 6-OH products. It has been applied for the synthesis of four oligosaccharides related to the galactomannan from Aspergillus fumigatus. The assembly of target oligosaccharides containing both (1→5) and (1→6) linkages between galactofuranosyl residues was performed by applying terminal mannoside and digalactofuranoside blocks, forming a versatile approach toward fungal and bacterial carbohydrate antigens containing both 5-O- and 6-O-substituted galactofuranoside residues.
authors.affiliation: Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences , Leninsky Prospect 47, 119991 Moscow, Russian Federation.
authors.forename: Dmitry A
authors.initials: DA
authors.lastname: Argunov
authors.affiliation: Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences , Leninsky Prospect 47, 119991 Moscow, Russian Federation.
authors.forename: Vadim B
authors.initials: VB
authors.lastname: Krylov
authors.affiliation: Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences , Leninsky Prospect 47, 119991 Moscow, Russian Federation.
authors.forename: Nikolay E
authors.initials: NE
authors.lastname: Nifantiev