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44 Chapter 2 2 Hz, Ar-H), 7.36 – 7.17 (33H, m, Ar-H), 7.01 (2H, d, J = 9.0 Hz, OMP), 6.78 (2H, d, J = 9.1 Hz, OMP), 5.09 (1H, d, J = 11.6 Hz, CHH), 5.01 – 4.94 (2H, m, H-1, Gal-III; CHH), 4.86 (1H, d, J = 7.5 Hz, H-1, Glc-I), 4.81 – 4.56 (8H, m, 4x CH 2 ), 4.51 – 4.42 (2H, m, H-1, Gal-II; CHH), 4.40 – 4.27 (3H, m, CH 2 ; CHH), 4.24 (1H, d, J = 3.2 Hz, H-4, Gal-III), 4.09 – 3.95 (5H, m, H-4, Gal-II; H-4, Glc-I; H-6a, Gal-II; H-3, Gal-III; H-5, Gal-II), 3.79 (2H, d, J = 3.1 Hz, H-6, Glc-I), 3.76 (3H, s, CH 3 , OMP), 3.72 (2H, s, H-6, Gal-III), 3.70 – 3.61 (3H, m, H-2, Glc-I; H-5, Gal-III; H-2, Gal-III), 3.56 (1H, dd, J = 9.9, 7.7 Hz, H-2, Gal-II), 3.51 – 3.43 (2H, m, H-6b, Gal-II; H-5, Glc-I), 3.34 (1H, dd, J = 8.3, 5.5 Hz, H-3, Glc-I), 3.29 (1H, dd, J = 10.0, 2.7 Hz, H-3, Gal-II), 2.40 – 2.31 (1H, m, OH), 0.97 (9H, s, t-Bu), 0.90 (9H, s, t-Bu). 13 C NMR (101 MHz, CDCl 3 ) δ 155.2 (C, OMP), 151.6 (C, OMP), 139.3 (C, Ar), 138.4 (C, Ar), 138.4 (C, Ar), 138.4 (2 C, Ar), 138.2 (C, Ar), 138.1 (C, Ar), 128.4, 128.3, 128.3, 128.3, 128.2, 128.2, 128.1, 128.0, 127.9, 127.7, 127.7, 127.6, 127.6, 127.6, 127.5, 127.4, 127.3, 127.1, 118.4 (2x CH, OMP), 114.5 (2x CH, OMP), 103.1 (C-1, Gal-II), 102.7 (C-1, Glc-I), 99.4 (C-1, Gal-III), 82.7 (C-5, Gal-III), 81.6 (C-2, Glc-I), 81.1 (C-3, Gal-II), 79.0 (C-2, Gal-II), 77.3 (C-5, Gal-II), 75.5 (C-2, Gal-III), 75.3 (C-5, Glc-I), 75.1, 75.0, 75.0, 73.9 (C-4, Gal-III), 73.2 (C-4, Glc-I), 73.1 (C-3, Glc-I), 73.0, 72.3, 70.1 (C-3, Gal-III), 68.4 (C-6, Glc-I), 67.5 (C-6, Gal, II), 67.1 (C-4, Gal-II), 66.7 (C-6, Gal-III), 55.6 (CH 3 , OMP), 27.5 (CH 3 , t-Bu), 27.2 (CH 3 , t-Bu), 23.2 (C, t-Bu), 20.6 (C, t-Bu). ESI HRMS (m/z): [M + NH 4 ] + calcd for C 82 H 96 O 17 Si, 1398.6755; found 1398.6760. [α] 25/589 = 54.2° (C = 0.05; CHCl 3 ). N-(Benzyl)-benzyloxycarbonyl-5-aminopentyl 2-O-benzyl-3-O-(2-naphthyl)methyl- 4 , 6 -O- d i - te r t- but y l s i l aned i y l - β -D- galactopyranosyl-(1 → 4)-2,3,6-tri-O- benzyl-β-D-galactopyranosyl-(1 → 4)-2,3,6- tri-O-benzyl-β-D-glucopyranoside (15b). A mixture of acceptor 12b (189 mg, 0.19 mmol), donor 11 (147 mg, 0.23 mmol) and 4 Å molecular sieves was s�rred in DCM (1.5 mL) for 1 h. The reac�on mixture was cooled to -30°C and N-iodosuccinimide (86 mg, 0.38 mmol) and triflic acid (1.7 µL, 0.02 mmol) were added. A�er 20 min the reac�on was quenched with Et 3 N, filtered over a pad of Celite and concentrated in vacuo . The obtained residue was purified by silica gel chromatography using Toluene:EtOAc (1:0 to 5:1 v/v) as the eluent to afford compound 15b (197 mg, 60%). 1 H NMR (400 MHz, CDCl 3 ) δ 7.95 – 7.64 (m, 4H, Ar-H), 7.54 – 6.79 (48H, m, Ar-H), 5.15 (2H, d, J = 6.3 Hz), 5.06 (1H, d, J = 11.1 Hz), 4.97 (1H, d, J = 3.4 Hz, H-1, Gal-III), 4.87 – 4.62 (7H, m), 4.62 – 4.38 (7H, m, H-1, Gal-II), 4.37 – 4.17 (4H, m, H-1, Glc-I), 4.16 – 4.07 (1H, m), 4.06 – 3.98 (2H, m, H-2, Gal-III), 3.98 – 3.63 (10H, m), 3.62 – 3.07 (10H, m, H-2, Gal-II, H-2, Glc-I), 1.68 – 1.40 (4H, m, 2x, CH 2 , pentyl), 1.40 – 1.16 (2H, m, CH 2 ¸ pentyl), 1.00 (9H, s, t-Bu), 0.97 (9H, s, t-Bu). 13 C NMR (101 MHz, CDCl 3 ) δ 139.3, 138.7, 138.7, 138.5, 138.3, 138.2, 136.7, 133.2, 132.9, 129.0, 128.5, 128.4, 128.4, 128.3, 128.2, 128.2, 128.1, 127.9, 127.8, 127.7, 127.6, 127.6, 127.4, 127.4, 127.3, 126.0, 125.9, 125.9, 125.6, 125.3, 103.5 (C-1, Glc-I), 102.9 (C-1, Gal-II), 100.1 (C-1, Gal-III), 82.5, 81.7 (C-2, Glc-I), 81.1, 79.0 (C-2, Gal-II), 78.0, 77.2, 75.1, 75.0, 74.9, 74.9, 74.2, 73.6 (C-2, Gal- III), 73.1, 73.1, 72.1, 71.2, 70.6, 70.1, 69.7, 68.3, 67.6, 67.5, 67.1, 67.1, 50.2, 47.2, 46.2, 29.4, 27.6 (CH 3 , t-Bu), 27.6, 27.3 (CH 3 , t-Bu), 23.3 (C, t-Bu), 20.7 (C, t-Bu). [α] 25/589 = -23.5° (C = 0.02; CHCl 3 ). O O O NapO BnO O O OBn BnO OBn O O O OBn BnO BnO Si NBnCbz