Enzymatic esterification and de-esterification of carbohydrates: synthesis of a naturally occurring rhamnopyranoside of p-hydroxybenzaldehyde and a systematic investigation of lipase-catalysed acylation of selected arylpyranosides

Abstract

The regiocontrolled esterification and de-esterification of mono- and di-saccharides is reviewed. New results involving the enzyme-catalysed regioselective acylation of ribo-110, arabino-112, 119, xylo-111, and rhamnopyranosides 116, 118(as well as two arylpyranosides 125 and 136), are reported. This methodology is then applied to the total synthesis of the naturally occurring rhamnopyranoside 4-(4-O-acetyl-α-L-rhamnosyloxy)benzaldehyde 122.