Phytoalexin elicitor hexasaccharide

The versatility of this methodology was demonstrated by its application to the synthesis of biologically relevant branched oligosaccharides, such as the phytoalexin elicitor hexasaccharide [124], [126], [127], a trisaccharide part of the Escherichia coli K26 antigen [122] and the trisaccharide repeating unit of the 02 antigen occurring in the lipopolisaccharide of Stenotrophomonas maltophilia [128]. 

Soybean plants can produce the antibiotic phytoalexin when exposed to a fungal /1-glucan. A phytoalexin elicitor hexasaccharide was synthesized by automation using glycosyl phosphate building blocks (Scheme 7). The functionalized resin was submitted to building blocks in a five-fold excess with stoichiometric amounts of trimethylsilyl trifluoromethanesulfonate for 15 minutes at - 15 °C. The resin was washed and treated with hydrazine to affect the deprotection of the C6 hydroxyl. The sequence was repeated three times,... 

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