Experimental study demonstrates regioselective lipase-catalyzed acylation of methyl glycosides with glyceric acid esters, indicating an efficient route to carbohydrate-based specialty esters.
The lipase‐catalyzed regioselective acylation of methyl α‐D‐galacto‐, ‐gluco‐ and ‐mannopyranosides with isopropylidene‐protected (R)‐ and (S)‐glyceric acid methyl esters in organic solvents is presented. Factors affecting the formation of the 6‐O‐mono‐ and 2,6‐O‐diacylated products are examined and preparative‐scale reactions are detailed. In addition, studies on partially protected methyl α‐D‐galactopyranosides are presented, with the 3,4‐O‐isopropylidene protected compound leading exclusively to the formation of the 6‐O‐monoacylated product even at high substrate concentrations. Application of acidic resin in methanol allows removal of the isopropylidene protection groups without disturbing the ester bond at C‐6.
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Sundell et al. (2013) studied this question.
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