De novo asymmetric synthesis of a 6-O-methyl-D-glycero-L- gluco-heptopyranose-derived thioglycoside for the preparation of Campylobacter jejuni NCTC11168 capsular polysaccharide fragments

• Author(s) / Creator(s)

  • Todd L. Lowary
  • Roger A. Ashmus
  • George A. O'Doherty
  • Ying Jie Lim
  • Anushka B. Jayasuriya

• An enantioselective de novo synthesis of a thioglycoside derivative of the 6-O-methyl-D-glycero- L-gluco-heptopyranose residue found in the Campylobacter jejuni NCTC11168 (HS:2) capsular polysaccharide is reported. The compound is obtained from a furfural-derived chiral diol in 11 steps. Notably, compared to the only previous synthesis of this molecule, this approach significantly reduces the number of purification steps required to obtain the target.

• Date created

  2016-03-17

• Subjects / Keywords

  • Carbohydrate

• Type of Item

  Article (Published)

• DOI

  https://doi.org/10.7939/R3K06XG2T

• License

  Attribution-NonCommercial-NoDerivatives 4.0 International