Decanoic Acid → methyl 6-O-decanoyl-D-glucopyranoside

Participants

Reaction Steps

Methyl-D-glucopyranoside (a 2:3 mixture of the α- and β-anomers) (24 g, 0.12 mol, prepared according to Example 6) was esterified with decanoic acid (43 g, 0.25 mol) by the procedure described in Example 1 using 2.4 g of an immobilized lipase (derived from Candida antarctica). After 17 hours the enzyme was removed by filtration (at 80° C.) HPLC analysis of the crude product showed 77% of the title compound, 15% diesters and 8% methyl-D-glucopyranoside. Part of the crude product was purified by chromatography, yielding 39.4 g (59%) of the title compound which was identified by NMR spectroscopy.

Provenance & Evidence