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

Phenylpropanoid Glycoside Analogues: Enzymatic Synthesis, Antioxidant Activity and Theoretical Study of Their Free Radical Scavenger Mechanism

“…The traditional chemical synthesis procedures result in low yields, require a considerable number of steps and require protection of the functional groups. Moreover, total yields observed for the enzymatic synthesis of PPGs (25%) were better than those previously reported and were accomplished in only two steps [5], [6], [11]–[18].…”

“…Several chemical pathways have been described for the synthesis of PPGs. Nevertheless, the requirement of protection and deprotection steps for their synthesis, also requiring stereochemical and regiochemical reactions result in non-sustainable, low yield and time consuming processes [5], [6], [11]–[18]. During the last two decades, biocatalysis has become a valuable tool in organic synthesis due to the chemo-, regio- and stereoselectivity of the enzymatic reactions, as well as their high specificity and mild reaction conditions.…”

Plantamajoside — A current review

“…Syringalide B was synthesized through a common intermediate, using a benzyl-moiety as a temporary protecting group following a shorter route together with another polyphenolic glycoside-grayanoside A (Das et al, 2007). The synthesis of arenarioside, a benzyl-protected analogue of a trisaccharide phenylpropanoid glycoside, was carried out by Zhou et al (2006). This polyphenolic glycoside was synthesized through two different routes from D-glucose and it was the first approach to the synthesis of a trisaccharide phenylpropanoid glycoside, although the benzyl-protecting group in the backbone of arenarioside analogue could not be removed by conventional debenzylation procedures (Zhou et al, 2006).…”

A selective and mild glycosylation method of natural phenolic alcohols

“…The most frequently used protocol under Koenigs–Knorr conditions is represented by the reaction of an acetobromoglucose and (4- O -benzyloxyphenyl)alkyl alcohol catalysed by Ag salts [ 9 , 18 ]. The final removal of the benzyl protecting group from the phenolic function of the aglycone by catalytic reduction can be however problematic in the case of more complex molecules containing for example double bonds (e.g., arenarioside) [ 30 ]. Isoconiferin ( 3 ) has been prepared mainly by the trichloroacetimidate method [ 20 – 21 ] using 4- O -acetylated coniferyl alcohol as the acceptor.…”