Ammonia → 4-{2-[4-(2-acetamido-2-deoxy-beta-D-glucopyranosyloxy)-3-methoxyphenyl]-vinyl}-1-methylquinolinium iodide

関与物質

反応手順

A stirred suspension of 4-formyl-2-methoxyphenyl 2-acetamido-2deoxy-β-D-glucopyranoside (1b)(0.25 g, 0.70 mmol), 1,4-dimethylquinolinium iodide (0.20 g, 0.70 mmol) in ethanol (20 ml) containing ammonium acetate (0.16 g, 2.1 mmol) and ammonia (conc.) (0.12 ml) was heated at 60°-70° C. The mixture soon turned orange and reaction was complete after 1.5 h as indicated by t.l.c. (chloroform-methanol, 5:4). The solid material was filtered off and washed sequentially with ethanol, acetone and ether to give (23b) as a fine yellow solid {0.34 g, 78%, m.p. 207°-212° C. (decomp.), [α]D +28° (c 1, DMOS)}(Found: C, 52.12; H, 5.01; N, 4.78. C27H31IN2O7 calc. C, 52.10; H, 5.02; N, 4.50%).

情報源と証拠