Towards the synthesis of glucose-containing fluorous oligosaccharides

• Author / Creator

  Mandal, Santu

• Fluorous phase chemistry is an emerging field in terms of new separation techniques. A highly fluorinated compound tends to dissolve in a fluorinated solvent rather than in a common organic solvent. Fluorophilic solid phase separation (F-SPE) techniques are also well established. Our goal is to explore the fluorous binding ability of highly fluorinated cyclic and acyclic glucopyranoside oligosaccharides against fluorinated lipids. For this purpose we have selected two families of targets: fluorinated cyclodextrins, α-(1→4)-linked cyclic glucose-containing oligosaccharides, and their open chain counterparts. Fluorinated cyclodextrins have previously been synthesized and shown to bind to p-trifluoromethyl phenol and inspiration for the latter class of compounds comes from bacteria. Some mycobacteria produce α-(1→4)-linked 6-O-methylated glucopyranose residues. These species form 1:1 complexes with long-chain fatty acids and acyl-coenzyme A derivatives in vitro. We envisioned that fluorinated derivatives of these molecules might bind to fluorinated lipids. We developed synthetic routes to prepare fluorinated oligosaccharides with variable number of glucopyranose residues. Our synthetic approach was focused on using cyclodextrins as the starting materials. These compounds were synthesized through a route that does not require protecting group chemistry. These cyclic molecules will serve as the precursors to the acyclic molecules through the use of a reported cyclodextrin cleavage method. In addition, we explore the preparation of derivatives from a bottom-up approach via the synthesis of mono- and disaccharide derivatives containing fluorinated moieties.

• Subjects / Keywords

  • Glucose-containing
  • Synthesis
  • Fluorous
  • Oligosaccharide

• Graduation date

  Spring 2014

• Type of Item

  Thesis

• Degree

  Master of Science

• DOI

  https://doi.org/10.7939/R38G8FT9P

• License

  This thesis is made available by the University of Alberta Libraries with permission of the copyright owner solely for non-commercial purposes. This thesis, or any portion thereof, may not otherwise be copied or reproduced without the written consent of the copyright owner, except to the extent permitted by Canadian copyright law.