α-Selective Xylofuranosylation Using a 2,3-O-Xylylene Protected Donor

• Author / Creator

  Zhang, Li

• Furanose-containing molecules are widespread in nature and have been identified as important constituents of glycoconjugates from numerous pathogenic microorganisms. Although significant advances in the synthesis of 1,2-cis-glycofuranosides have been made, there are still some challenges. In particular, almost no studies investigating the synthesis of 1,2-cis-xylofuranosides have been carried out. Previous studies by our group have demonstrated that the utility 2,3-O-xylylene protected arabinofuranosyl donors in the synthesis of 1,2-cis-(β)-arabinofuranosides. Therefore, we wanted to expand this methodology to the synthesis of 1,2-cis-(α)-xylofuranosides. Several 2,3-O-xylylene protected xylofuranosyl donors were synthesized, glycosylations employing them have been optimized and the substrate scope of the reaction has been explored. Finally, to demonstrate the utility of the methodology, a 5-deoxy-5-methylthio-α-xylofuranose- (MTX) containing pentasaccharide fragment of mycobacterial LAM was synthesized.

• Subjects / Keywords

  • 1,2-cis glycosylation
  • 5-deoxy-5-methylthio-xylofuranose
  • xylylene
  • Xylofuranosylation

• Graduation date

  Spring 2016

• Type of Item

  Thesis

• Degree

  Master of Science

• DOI

  https://doi.org/10.7939/R3SF2MT7T

• 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.