Octanoic Acid → ethyl 6-O-octanoyl-D-glucopyranoside

Reaktionsgleichung

[O:1]([CH2:13][CH3:14])[CH:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4].[C:15](O)(=[O:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>CCCCCC.C1C(CCCCC(N)=O)SSC1>[C:15]([O:12][CH2:11][C@H:9]1[O:10][CH:2]([O:1][CH2:13][CH3:14])[C@H:3]([OH:4])[C@@H:5]([OH:6])[C@@H:7]1[OH:8])(=[O:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Komponenten

Versuchsvorschrift

To a suspension of ethyl D-glucopyranoside (500 g, 2.4 mol prepared according to example 10) and octanoic acid (520 g, 3.6 mol) in hexane (1000 ml) in a stirred batch reactor at 70° C. (reflux) was added immobilized lipase (5 g Lipozyme™, commercial available NOVO lipase prepared from a Mucor Miehei). Stirring was continued and the produced water was removed by azeotropic distillation. The progress of the reaction was followed by HPLC. As the product was being formed, the suspension gradually became a homogeneous solution (after 12 hours). After 52 hours the enzyme was removed by filtration and the solvent removed in vacuo. Excess fatty acid was removed by repeated molecular distillation giving a crude product (790 g, 91% monoester, 8% diester and 1% ethyl D-glucopyranoside). H1 and 13C NMR-spectra of the purified product were in accordance with the spectra for the pure α- and β-anomers given in tables 4 a/4 b.