Full Papers
(m, 5H), 1.37–1.17 (m, 65H), 0.89 ppm (t, J=6.5 Hz, 6H); 13C NMR
(75 MHz, CDCl3): d=173.0, 159.4, 159.3, 159.2, 138.7, 131.0, 130.9,
130.8, 130.7, 129.8, 129.7, 129.6, 129.2, 128.4, 128.3, 127.7, 113.9,
113.9, 99.9, 79.9, 78.8, 78.4, 76.4, 75.1, 74.8, 73.4, 73.3, 73.2, 72.7,
71.4, 70.1, 69.7, 69.1, 55.3, 55.3, 50.4, 36.8, 32.1, 30.0, 29.9, 29.8,
29.8, 29.7, 29.6, 29.5, 29.4, 29.3, 26.2, 25.8, 24.9, 22.8, 14.3 ppm;
HRMS (ESI-MS) m/z: calcd for C97H146NO14 [M+H]+ 1549.0738,
found 1549.0737; Rf (petroleum ether/EtOAc 70:30): 0.48.
130.8, 130.0, 129.9, 129.7, 129.6, 129.5, 129.1, 128.5, 128.4, 125.7,
113.9, 113.8, 99.8, 79.9, 78.7, 78.4, 76.4, 75.8, 73.6, 73.4, 73.3, 72.4,
71.4, 70.1, 68.9, 55.4, 55.3, 50.4, 36.8, 36.1, 32.1, 31.5, 30.2, 30.0,
29.9, 29.8, 29.7, 29.6, 29.5, 29.4, 26.2, 26.0, 25.8, 22.8, 14.3 ppm;
HRMS (ESI-MS) m/z: calcd for C101H154NO14 [M+H]+ 1605.1364,
found 1605.1362; Rf (petroleum ether/EtOAc 70:30): 0.45.
(2S,3S,4R)-1-[2,3,6-Tri-O-(p-methoxybenzyl)-4-O-(6-phenylhexyl)-
a-d-galactopyranosyloxy]-2-hexacosanoylamino-3,4-di-O-(p-me-
thoxybenzyl)octadecane (14e): Following general procedure D,
13e (0.216 g, 0.171 mmol) afforded 14e (0.197 g, 71%) as a yellow
wax. 1H NMR (300 MHz, CDCl3): d=7.35–7.12 (m, 15H), 6.92–6.72
(m, 10H), 6.14 (d, J=8.5 Hz, 1H), 4.83 (d, J=3.4 Hz, 1H), 4.73 (t, J=
10.4 Hz, 2H), 4.67 (s, 2H), 4.58 (d, J=11.1 Hz, 1H), 4.54 (d, J=
11.1 Hz, 1H), 4.48 (t, J=10.4 Hz, 2H), 4.39 (d, J=11.2 Hz, 1H), 4.36
(d, J=11.1 Hz, 1H), 4.17 (m, 1H), 4.04–3.82 (m, 6H), 3.79 (s, 3H),
3.77 (s, 9H), 3.76–3.71 (m, 2H), 3.73 (s, 3H), 3.64–3.37 (m, 4H), 2.60
(t, J=7.8 Hz, 2H), 1.97 (m, 2H), 1.70–1.40 (m, 10H), 1.38–1.19 (m,
70H), 0.91 ppm (t, J=6.4 Hz, 6H); 13C NMR (75 MHz, CDCl3): d=
172.9, 159.4, 159.3, 159.2, 159.1, 142.8, 130.9, 130.8, 130.7, 129.8,
129.7, 129.6, 129.5, 129.1, 128.4, 128.3, 125.7, 113.9, 113.8, 99.8,
79.8, 78.3, 76.3, 75.7, 73.5, 73.3, 73.2, 72.4, 71.3, 70.1, 68.8, 55.3,
55.2, 50.3, 36.7, 36.0, 32.0, 31.6, 30.3, 29.9, 29.8, 29.7, 29.6, 29.5,
29.4, 29.2, 26.1, 26.0, 25.8, 22.7, 14.2 ppm; HRMS (ESI-MS) m/z:
calcd for C102H156NO14 [M+H]+ 1619.1520, found 1619.1513; Rf (pe-
troleum ether/EtOAc 70:30): 0.40.
(2S,3S,4R)-1-[2,3,6-Tri-O-(p-methoxybenzyl)-4-O-(3-phenylprop-
yl)-a-d-galactopyranosyloxy]-2-hexacosanoylamino-3,4-di-O-(p-
methoxybenzyl)octadecane (14b): Following general procedure
D, 13b (0.166 g, 0.136 mmol) afforded 14b (0.175 g, 81%) as a
yellow wax. 1H NMR (300 MHz, CDCl3): d=7.32–7.12 (m, 15H),
6.91–6.72 (m, 10H), 6.12 (d, J=8.5 Hz, 1H), 4.84 (d, J=3.6 Hz, 1H),
4.74 (d, J=11.3 Hz, 1H), 4.71 (d, J=11.2 Hz, 1H), 4.65 (dd, J=15.8,
11.0 Hz, 2H), 4.59 (d, J=11.3 Hz, 1H), 4.54 (d, J=11.1 Hz, 1H), 4.48
(d, J=11.6 Hz, 1H), 4.47 (d, J=11.0 Hz, 1H), 4.37 (d, J=11.1 Hz,
2H), 4.17 (m, 1H), 4.05–3.88 (m, 4H), 3.87–3.80 (m, 2H), 3.79 (s,
6H), 3.77 (s, 3H), 3.76 (s, 3H), 3.76–3.73 (m, 2H), 3.72 (s, 3H), 3.63–
3.43 (m, 4H), 2.64 (t, J=7.6 Hz, 2H), 2.04–1.80 (m, 6H), 1.71–1.40
(m, 8H), 1.35–1.17 (m, 62H), 0.90 ppm (t, J=6.8 Hz, 6H); 13C NMR
(75 MHz, CDCl3): d=172.9, 159.5, 159.3, 159.2, 159.1, 142.3, 131.0,
130.9, 130.8, 130.7, 129.8, 129.7, 129.6, 129.6, 129.2, 128.6, 128.4,
125.8, 113.9, 113.8, 99.8, 79.8, 78.6, 78.4, 76.2, 75.9, 73.4, 73.3, 72.8,
72.5, 71.4, 70.1, 69.5, 68.8, 55.3, 55.3, 50.4, 36.8, 32.5, 32.1, 32.0,
30.0, 29.9, 29.8, 29.8, 29.7, 29.6, 29.5, 26.2, 25.8, 22.8, 14.3 ppm;
HRMS (ESI-MS) m/z: calcd for C99H149NO14 [M+H]+ 1577.1051,
found 1577.1057; Rf (petroleum ether/EtOAc 70:30): 0.38.
(2S,3S,4R)-1-{2,3,6-Tri-O-(p-methoxybenzyl)-4-O-[3-(4-methylphe-
nyl)propyl]-a-d-galactopyranosyloxy}-2-hexacosanoylamino-3,4-
di-O-(p-methoxybenzyl)octadecane (14 f): Following general pro-
cedure D, 13 f (0.209 g, 0.169 mmol) afforded 14 f (0.193 g, 72%)
(2S,3S,4R)-1-[2,3,6-Tri-O-(p-methoxybenzyl)-4-O-(4-phenylbutyl)-
a-d-galactopyranosyloxy]-2-hexacosanoylamino-3,4-di-O-(p-me-
thoxybenzyl)octadecane (14c): Following general procedure D,
13c (0.189 g, 0.153 mmol) afforded 14c (0.196 g, 80%) as a yellow
wax. 1H NMR (300 MHz, CDCl3): d=7.35–7.08 (m, 15H), 6.91–6.71
(m, 10H), 6.12 (d, J=8.5 Hz, 1H), 4.81 (d, J=3.3 Hz, 1H), 4.73 (d,
J=11.5 Hz, 1H), 4.70 (d, J=10.8 Hz, 1H), 4.67 (dd, J=15.1, 11.3 Hz,
2H), 4.56 (d, J=11.3 Hz, 1H), 4.54 (d, J=11.2 Hz, 1H), 4.48 (d, J=
11.5 Hz, 1H), 4.47 (d, J=11.0 Hz, 1H), 4.36 (d, J=11.2 Hz, 2H), 4.17
(m, 1H), 4.03–3.88 (m, 4H), 3.87–3.80 (m, 2H), 3.79 (s, 3H), 3.78 (s,
6H), 3.77 (s, 3H), 3.76–3.72 (m, 2H), 3.74 (s, 3H), 3.62–3.40 (m, 4H),
2.60 (t, J=7.4 Hz, 2H), 1.97 (m, 3H), 1.73–1.43 (m, 11H), 1.38–1.17
(m, 64H), 0.90 ppm (t, J=6.6 Hz, 6H); 13C NMR (75 MHz, CDCl3): d=
172.9, 159.4, 159.3, 159.2, 159.1, 142.7, 131.0, 130.9, 130.9, 130.8,
129.9, 129.7, 129.6, 129.5, 129.1, 128.5, 128.3, 125.8, 113.9, 113.8,
99.8, 79.9, 78.7, 78.4, 76.2, 75.8, 73.4, 73.3, 72.5, 71.4, 70.1, 69.5,
68.8, 55.3, 55.2, 50.4, 36.8, 35.8, 32.1, 30.0, 29.9, 29.8, 29.7, 29.6,
29.5, 28.1, 26.2, 25.8, 22.8, 14.2 ppm; HRMS (ESI-MS) m/z: calcd for
C100H152NO14 [M+H]+ 1591.1207, found 1591.1221; Rf (petroleum
ether/EtOAc 70:30): 0.39.
1
as a yellow wax. H NMR (300 MHz, CDCl3): d=7.32–7.15 (m, 10H),
7.07 (s, 4H), 6.90–6.75 (m, 10H), 6.14 (d, J=8.6 Hz, 1H), 4.85 (d, J=
3.6 Hz, 1H), 4.76 (d, J=11.1 Hz, 1H), 4.73 (d, J=11.3 Hz, 1H), 4.67
(dd, J=15.6, 11.3 Hz, 2H), 4.61 (d, J=11.3 Hz, 1H), 4.56 (d, J=
11.3 Hz, 1H), 4.50 (d, J=11.4 Hz, 1H), 4.49 (d, J=11.0 Hz, 1H), 4.39
(d, J=11.7 Hz, 1H), 4.38 (d, J=11.7 Hz, 1H), 4.18 (m, 1H), 4.06–3.90
(m, 4H), 3.89–3.80 (m, 2H), 3.80 (s, 6H), 3.78 (s, 6H), 3.77–3.73 (m,
2H), 3.74 (s, 3H), 3.65–3.43 (m, 4H), 2.62 (t, J=7.7 Hz, 2H), 2.33 (s,
3H), 2.07–1.81 (m, 4H), 1.71–1.42 (m, 6H), 1.37–1.20 (m, 66H),
0.91 ppm (t, J=6.8 Hz, 6H); 13C NMR (75 MHz, CDCl3): d=172.8,
159.4, 159.3, 159.2, 159.2, 139.1, 135.1, 130.9, 130.8, 130.7, 129.8,
129.7, 129.6, 129.5, 129.4, 129.1, 129.0, 128.4, 113.9, 113.8, 99.8,
79.8, 78.6, 78.4, 76.1, 75.8, 73.3, 73.2, 72.8, 72.4, 71.3, 70.1, 69.5,
68.8, 55.3, 55.2, 50.3, 36.8, 32.0, 30.0, 29.8, 29.7, 29.6, 29.5, 29.4,
29.3, 26.1, 25.8, 22.8, 21.1, 14.2 ppm; HRMS (ESI-MS) m/z: calcd for
C100H152NO14 [M+H]+ 1591.1207, found 1591.1210; Rf (petroleum
ether/EtOAc 70:30): 0.39.
(2S,3S,4R)-1-{2,3,6-Tri-O-(p-methoxybenzyl)-4-O-[3-(4-chlorophe-
nyl)propyl]-a-d-galactopyranosyloxy}-2-hexacosanoylamino-3,4-
di-O-(p-methoxybenzyl)octadecane (14g): Following general pro-
cedure D, 13g (0.196 g, 0.156 mmol) afforded 14g (0.196 g, 78%)
(2S,3S,4R)-1-[2,3,6-Tri-O-(p-methoxybenzyl)-4-O-(5-phenylpentyl)-
a-d-galactopyranosyloxy]-2-hexacosanoylamino-3,4-di-O-(p-me-
thoxybenzyl)octadecane (14d): Following general procedure D,
13d (0.201 g, 0.160 mmol) afforded 14d (0.190 g, 74%) as a yellow
wax. 1H NMR (300 MHz, CDCl3): d=7.33–7.11 (m, 15H), 6.91–6.73
(m, 10H), 6.10 (d, J=8.6 Hz, 1H), 4.83 (d, J=3.6 Hz, 1H), 4.73 (d,
J=11.3 Hz, 1H), 4.70 (d, J=10.9 Hz, 1H), 4.66 (dd, J=13.4, 11.5 Hz,
2H), 4.56 (d, J=11.4 Hz, 1H), 4.53 (d, J=11.3 Hz, 1H), 4.49 (d, J=
11.7 Hz, 1H), 4.46 (d, J=11.0 Hz, 1H), 4.37 (d, J=11.5 Hz, 1H), 4.36
(d, J=11.2 Hz, 1H), 4.16 (m, 1H), 4.04–3.80 (m, 6H), 3.79 (s, 3H),
3.78 (s, 3H), 3.77 (s, 6H), 3.76–3.70 (m, 2H), 3.74 (s, 3H), 3.62–3.37
(m, 4H), 2.59 (t, J=7.6 Hz, 2H), 1.96 (m, 3H), 1.69–1.46 (m, 9H),
1.39–1.17 (m, 68H), 0.90 ppm (t, J=6.7 Hz, 6H); 13C NMR (75 MHz,
CDCl3): d=172.9, 159.4, 159.3, 159.2, 159.1, 142.8, 131.0, 130.9,
1
as a yellow wax. H NMR (300 MHz, CDCl3): d=7.31–7.14 (m, 12H),
7.10–7.02 (m, 2H), 6.90–6.72 (m, 10H), 6.10 (d, J=8.4 Hz, 1H), 4.84
(d, J=3.6 Hz, 1H), 4.74 (d, J=11.3 Hz, 1H), 4.71 (d, J=10.9 Hz, 1H),
4.65 (dd, J=19.6, 11.3 Hz, 2H), 4.60 (d, J=11.5 Hz, 1H), 4.55 (d, J=
11.3 Hz, 1H), 4.49 (d, J=11.5 Hz, 1H), 4.47 (d, J=11.2 Hz, 1H), 4.38
(d, J=11.3 Hz, 1H), 4.36 (d, J=11.5 Hz, 1H), 4.19 (m, 1H), 4.05–3.89
(m, 3H), 3.88–3.81 (m, 3H), 3.80 (s, 3H), 3.79 (s, 3H), 3.78–3.73 (m,
2H), 3.77 (s, 6H), 3.72 (s, 3H), 3.62–3.39 (m, 4H), 2.59 (t, J=7.6 Hz,
2H), 2.06–1.74 (m, 4H), 1.72–1.39 (m, 6H), 1.36–1.17 (m, 66H),
0.89 ppm (t, J=6.7 Hz, 6H); 13C NMR (75 MHz, CDCl3): d=172.9,
159.5, 159.3, 159.2, 140.7, 131.4, 130.9, 130.8, 130.7, 129.9, 129.8,
129.7, 129.6, 129.5, 129.2, 128.4, 113.9, 113.8, 99.7, 79.8, 78.6, 78.5,
ChemMedChem 2018, 13, 1 – 23
15
ꢀ 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
&
These are not the final page numbers! ÞÞ