Concise synthesis of the trisaccharide repeating unit of the O-polysaccharide from Aeromonas hydrophila A19 (O:14)

• Synthesis of a trisaccharide having one α-glucopyranoside.
• Use of H2SO4–silica in conjunction with N-iodosuccinimide for the activation of thioglycosides.
• Stereoselective glycosylations in excellent yields to provide the target oligosaccharide in good quantity.

Chemical synthesis of the trisaccharide repeating unit of the O-polysaccharide from Aeromonas hydrophila A19 (O:14) is reported in the form of its p-methoxyphenyl glycosides. Suitably protected monosaccharide synthons were prepared either by literature procedure or by strategies developed in house. Stereoselective glycosylations were accomplished by the activation of thioglycosides using N-iodosuccinimide in conjunction with H2SO4–silica in good to excellent yields.

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