title: Influence of silyl protections on the anomeric reactivity of galactofuranosyl thioglycosides and application of the silylated thiogalactofuranosides to one-pot synthesis of diverse β-D-oligogalactofuranosides.
abstract: We describe in this paper the tuning effect of silyl protecting groups on the donor reactivity of galactofuranosyl phenyl thioglycosides. Silyl ethers on the galactofuranose ring are found to have an arming effect on the glycosylation reactivity, but the cyclic 3,5-acetal protecting group decreases the reactivity. The reactive phenyl 2,6-di-O-Bz-3,5-di-O-TBS-1-thio-β-d-galactofuranoside 3 is proved to be a useful glycosyl building block. By taking advantage of this donor, we achieved the highly efficient one-pot solution-phase assembly of a panel of β-d-galactofuranosyl tri- and tetrasaccharides possessing diverse glycosidic linkages.
authors.affiliation: Key Laboratory of Drug Targeting, Ministry of Education, and Department of Chemistry of Medicinal Natural Products, West China School of Pharmacy, Sichuan University , Chengdu 610041, P. R. China.
authors.forename: Shuai
authors.initials: S
authors.lastname: Wang
authors.forename: Xue
authors.initials: X
authors.lastname: Meng
authors.forename: Wei
authors.initials: W
authors.lastname: Huang
authors.forename: Jin-Song
authors.initials: JS
authors.lastname: Yang
mesh_terms: D004987:Ethers / Q000737:chemistry*; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D012821:Silanes / Q000737:chemistry*; D013865:Thioglycosides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D004987:Ethers; D009844:Oligosaccharides; D012821:Silanes; D013865:Thioglycosides