Reaction Steps
The title compound was prepared as a white foam (0.225 g, 72%) from 4-chloro-benzoic acid 6-(3-acetylamino-4-chloro-benzyloxy)-3-(7,8-dihydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-4,5-dihydroxy-tetrahydro-pyran-2-ylmethyl ester using a procedure similar to Example 25, mp 114-115° C.; 1H NMR (DMSO-d6) δ1.94 (s, 3H), 1.95 (s, 3H), 1.98 (s, 3H), 1.99 (s, 3H), 2.05 (s, 3H), 3.62 (t, J=9.2 Hz, 1H), 3.68-3.74 (m, 1H), 3.79 (dd, J=4.2, 9.2 Hz, 1H), 3.86 (t, J=9.4 Hz, 1H), 4.13-4.19 (m, 1H), 4.18 (q, J=9.4, 1H), 4.47 (dd, J=3.5, 12.3 Hz, 1H), 4.63 (ABq, J=12.7 Hz, Δδ=0.14, 2H), 4.66 (d, J=10.8 Hz, 1H), 4.79 (dd, J=8.1, 9.2 Hz, 1H), 4.86-4.91 (m, 2H), 5.26 (t, J=9.9 Hz, 1H), 5.32-5.38 (m, 2H), 5.54 (s, 1H), 7.05 (dd, J=1.8, 8.3 Hz, 1H), 7.27-7.31 (m, 2H), 7.32-7.36 (m, 3H), 7.42 (d, J=8.3 Hz, 1H), 7.58-7.63 (m, 3H), 8.02-8.06 (m, 2H), 9.49 (s, 1H); IR (KBr) 3410, 2950, 2860, 1755, 1690, 1600, 1530, 1450, 1420, 1375, 1260, 1140, 1070, 1055, and 1030 cm−1; mass spectrum [(+) FAB], m/z 918/920/922 (M+H)+, 940/942/944 (M+Na)+; Anal. Calcd. for C43H45Cl2NO17.1.0 H2O: C, 55.13; H, 5.06; N, 1.50, Found: C, 54.77; H, 4.73; N, 1.45.
