Experimental synthesis demonstrates the stepwise assembly of an Albizia procera-derived trisaccharide, revealing unexpected conformational shifts reversible upon deprotection.
Chemical synthesis of a trisaccharide related to the cytotoxic triterpenoid saponins isolated from the bark of Albizia procera has been accomplished through a concise stepwise glycosylation strategy starting from commercially available D‐xylose, 2‐acetamido‐2‐deoxy‐D‐glucose and L‐arabinose. The target trisaccharide was designed with a 4‐methoxyphenyl (MP) aglycone to extend the scope of conversion to suitable glycoconjugates via selective removal of 4‐methoxyphenyl (MP) group. An unexpected phenomenon, i.e., the arabinosyl residue assumed the 1C4 conformation instead of the typical 4C1 form, was observed. Deprotection could restore the normal conformation.
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Liu et al. (2014) studied this question.
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