Toward solution-phase automated iterative synthesis: fluorous-tag assisted solution-phase synthesis of linear and branched mannose oligomers.
We report herein the first synthesis of linear and branched mannose oligosaccharides using fluorous-tag assistance with reagents and FSPE protocols that are amenable to automation. The particular fluorous linker proved to maintain solubility of the growing oligosaccharide chain such that identical reaction solvent conditions and purification protocols could be used between glycosylation and deprotection reactions, thereby rendering the procedures amenable to automation.
Jaipuri
Firoz A
FA
Department of Chemistry and Plant Sciences Institute, Gilman Hall, Iowa State University, Ames, IA 50011-3111, USA.
Pohl
Nicola L
NL
D002236:Carbohydrate Conformation; D003432:Cross-Linking Reagents / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D008358:Mannose / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry*; D044367:Phase Transition; D052616:Solid Phase Extraction; D012996:Solutions / Q000737:chemistry
D003432:Cross-Linking Reagents; D006845:Hydrocarbons, Fluorinated; D009844:Oligosaccharides; D012996:Solutions; D008358:Mannose