Octanoic Acid → α-D-Glucopyranoside, methyl, 6-octanoate

Participants

Reaction Steps

Methyl α-D-glucopyranoside (20.0 g, 0.10 mol, prepared according to Example 6), was esterified with octanoic acid (29.7 g, 0.21 mol) by the procedure described in Example 1 using 6.0 g of an immobilized lipase (from Candida antarctica) as a catalyst. After 36 hours HPLC analysis showed 77% conversion (65% monoester, 12% diester). The reaction was stopped by filtering off the enzyme. Part of the crude product was purified by chromatography yielding 10.7 g (32.4%) of the title compound which was identified by NMR spectroscopy.

Provenance & Evidence