69 (t, J = six.7, 1H), 3.59.67 (m, 4H), 3.43 (dt, J = 6.7, 9.eight,

69 (t, J = six.7, 1H), 3.59.67 (m, 4H), 3.43 (dt, J = 6.7, 9.eight, 1H), 1.52.60 (m, 2H), 1.40.52 (m
69 (t, J = six.7, 1H), 3.59.67 (m, 4H), 3.43 (dt, J = 6.7, 9.eight, 1H), 1.52.60 (m, 2H), 1.40.52 (m, 2H), 0.98.39 (m, 32H); 13 C1 H NMR (CDCl3 , 125 MHz) 166.9, 165.six, 165.four, 165.three, 165.2, 165.1, 164.9, 134.9, 133.four, 133.three, 133.2, 133.1, 133.05, 133.0, 129.eight, 129.75, 129.7, 129.65, 129.six, 129.45, 129.four, 129.three, 128.9, 128.85, 128.eight, 128.75, 128.7, 128.six, 128.5, 128.three, 128.2, 128.1, 101.5, one hundred.three, 76.0, 74.six, 72.three, 71.six, 71.five, 71.0, 70.5, 69.eight, 67.six, 67.3, 63.0, 61.1, 32.8, 29.7, 29.64, 29.63, 29.61, 29.60, 29.58, 29.56, 29.five, 29.42, 29.41, 29.3, 29.2, 25.7; IR max 2926, 2854, 2254, 1728, 1602, 1585, 1493, 1452, 1315, 1263, 1177, 1092, 1068, 1027, 1001, 908, 856, 802, 730, 706 cm ; HRMS (ESI) m/z [M H] calcd. for C81 H91 O19 , 1367.61491; located 1367.61305. 2 ,three ,4 ,six -Tetra-O-benzoyl– D -galactopyranosyl)-(1 four)-2,3-di-O-benzoyl-5benzoxycarbonyl-1-((20-oxoeicosyl-1-oxy)–Moveltipril supplier D-glucopyranoside (eight). A resolution of 22 (1.00 g, 731 ol) in CH2 Cl2 (14.six mL) was treated with DMP (467 mg, 1.ten mmol) plus the resulting mixture was stirred for 2 h at area temperature. A 10 aqueous Na2 S2 O3 answer (50 mL) was added, the aqueous phase was separated and SBP-3264 medchemexpress extracted with CH2 Cl2 (3 50 mL). The combined organic phases had been dried more than Na2 SO4 and concentrated in vacuo. The crude solution was purified by flash chromatography (n-hexane/EtOAc 82:18) to give 8 (890 mg, 652 ol, 89 ) as a colorless foam of mp 58 C; Rf = 0.29 (n-hexane/EtOAc 8:two); []24 D -5.eight (c 0.3, CHCl3 ); 1 H NMR (CDCl3 , 500 MHz) 9.76 (t, J = 2.0, 1H), 8.02.05 (m, 2H), 7.92.00 (m, 6H), 7.85.90 (m, 2H), 7.70.75 (m, 2H), 7.58.64 (m, 2H), 7.46.56 (m, 6H), 7.27.46 (m, 11H), 7.22 (t, J = 7.6, 2H), 7.12 (t, J = 7.6, 2H), five.73 (t, J = 9.3, 1H), 5.65 (d, J = three.7, 1H), five.54 (dd, J = 7.9, ten.4, 1H), five.42 (dd, J = 7.six, 9.eight, 1H), 5.33 (d, J = 11.9, 1H), five.27 (dd, J = three.four, ten.4, 1H), four.66.71 (m, 3H), 4.41 (t, J = 9.three, 1H), 4.09 (d, J = 9.5, 1H), 3.80 (dt, J = six.4, 9.8, 1H), three.67.72 (m, 1H), 3.59.66 (m, 2H), 3.43 (dt, J = 6.7, 9.8, 1H), two.42 (dt, J = 1.eight, 7.3, 2H), 1.62 (q, J = 7.2, 2H), 1.39.50 (m, 2H), 0.98.35 (m, 32H); 13 C1 H NMR (CDCl3 , 125 MHz) 203.three, 166.9, 165.six, 165.four, 165.three, 165.two, 165.1, 165.0, 134.9, 133.5, 133.4, 133.two, 133.15, 133.0, 130.0, 129.eight, 129.75, 129.70, 129.68, 129.6, 129.46, 129.44, 129.3, 128.89, 128.87, 128.85, 128.80, 128.7, 128.six, 128.5, 128.three, 128.24, 128.15, one hundred.six, one hundred.three, 76.0, 74.6, 72.three, 71.six, 71.five, 71.0, 70.six, 69.eight, 67.6, 67.three, 61.1, 43.9, 33.4, 29.69, 29.67, 29.66, 29.64, 29.58, 29.54, 29.45, 29.42, 29.35, 29.28, 29.25, 29.23, 29.15, 29.1, 25.7, 24.7; IR max 3064, 2924, 2853, 1726, 1602, 1585, 1493, 1451, 1315, 1261, 1177, 1091, 1067, 1026, 1001, 911, 855, 802, 746, 687 cm ; HRMS (ESI) m/z [M Na] calcd. for C81 H88 O19 Na , 1387.58120; discovered 1387.58412. two ,three ,4 ,6 -Tetra-O-benzoyl– D -galactopyranosyl)-(1 4)-2,3-di-O-benzoyl-5benzoxycarbonyl-1-(22-oxo-24-(S-tert-butylthiocarbonyl)-eicosa-20-enyl-1-oxy)–D -glucopyranoside (6). To a answer of phosphonate 9 (34.1 mg, 110 ol) in THF (1.35 mL) at 0 C was dropwise added a LiHMDS answer (220 , 1M in THF) and the resulting mixture was stirred for 30 min at area temperature, cooled to 0 C, and treated with a resolution of eight (one hundred mg, 73.2 ol) in THF (1.35 mL). Following stirring for an additional 16 h at room temperature, a saturated aqueous NH4 Cl resolution (20 mL) was added. The aqueous layer was separated and extracted with Et2 O (three 20 mL). The combined organic phases have been dried over Na2 SO4 and concentrated in vacuo. The crude product.