Synthesis of a benzyl-protected analog of arenarioside, a trisaccharide phenylpropanoid glycoside

A benzyl-protected analog of the phenylpropanoid glycoside arenarioside, (4-benzyloxyphenyl)ethyl α-l-rhamnopyranosyl-(1→3)-4-O-[(E)-3,4-di-O-benzyl-caffeoyl]-[β-d-xylopyranosyl-(1→6)]-β-d-glucopyranoside (22), was synthesized through two different routes from d-glucose. This is the first approach on the synthesis of a trisaccharide phenylpropanoid glycoside, although the benzyl-protecting group in the backbone of the arenarioside analog could not be removed by conventional debenzylation procedures.

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