title: Automated fluorous-assisted solution-phase synthesis of β-1,2-, 1,3-, and 1,6-mannan oligomers.
abstract: Automated solution-phase syntheses of β-1,2-, 1,3-, and 1,6-mannan oligomers have been accomplished by applying a β-directing C-5 carboxylate strategy. Fluorous-tag-assisted purification after each reaction cycle allowed the synthesis of short β-mannan oligomers with limited loading of glycosyl donor-as low as 3.0 equivalents for each glycosylation cycle. This study showed the capability of the automated solution-phase synthesis protocol for synthesizing various challenging glycosides, including use of a C-5 ester as a protecting group that could be converted under reductive conditions to a hydroxymethyl group for chain extension.
authors.affiliation: Department of Chemistry, Iowa State University, Ames, IA 50011, USA.
authors.forename: Shu-Lun
authors.initials: SL
authors.lastname: Tang
authors.affiliation: Department of Chemistry, Iowa State University, Ames, IA 50011, USA; Department of Chemistry, Indiana University, Bloomington, IN 47405, USA. Electronic address: npohl@indiana.edu.
authors.forename: Nicola L B
authors.initials: NLB
authors.lastname: Pohl
mesh_terms: D001331:Automation; D002264:Carboxylic Acids / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic; D005461:Fluorine / Q000737:chemistry*; D006031:Glycosylation; D008351:Mannans / Q000737:chemistry*; D009844:Oligosaccharides / Q000737:chemistry* / Q000378:metabolism*; D012996:Solutions
chemical_list: D002264:Carboxylic Acids; D008351:Mannans; D009844:Oligosaccharides; D012996:Solutions; D005461:Fluorine
keywords: Automated oligosaccharide synthesis; Fluorous-assisted synthesis; β-Mannan; β-Mannuronate