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.

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

The Journal of organic chemistry 2016 Apr 1

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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.

Citation

Roger A Ashmus, Anushka B Jayasuriya, Ying-Jie Lim, George A O'Doherty, Todd L Lowary. 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. The Journal of organic chemistry. 2016 Apr 1;81(7):3058-63