Diethyl Ether → 2-{2-[4-(beta-D-Galactopyranosyloxy)-3-methoxyphenyl]-vinyl}-3-methylbenzothiazolium tosylate

Beteiligte Stoffe

Reaktionsschritte

4-Formyl-3-methoxyphenyl β-D-galactopyranoside (1c)(3.14 g, 0.01 mol) was dissolved in hot methanol (20 ml) and 2,3-dimethylbenzothiazolium tosylate (3.35 g, 0.01 mol) was added followed by a drop of piperidine. The mixture was heated under reflux for 2 h, during which time it become strongly coloured. The reaction mixture was then cooled and ether (200 ml) was added to precipitate the product as an orange solid, which was well washed with methanol to give (26c){4.8 g, 80%, m.p. 147°-149° C., [α]D -10.4`0 (c 1, DMSO)}. (Found: C, 55.66; H, 5.28; N, 2.11. C30H34O11NS2Calc: C, 55.54; N, 5.28; N, 2.16.)

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