6
W. Shi et al.
633.3974
3.3.2 Compound 4b: 3-O-acetyl-30-(4-
(4-fluorophenyl)-1H-1,2,3-triazol-1-yl)
betulin
[M þ 1]þ
(calcd
for
C38H55N3O3S, 633.3964).
White solid, m.p. 142–145 C (uncor-
rected); 1H NMR (400 MHz, CDCl3) d
7.82–7.75 (m, 2H), 7.70 (s, 1H), 7.10
(t, J ¼ 8.7 Hz, 2H), 5.06 (s, 1H), 5.01–4.89
(m, 2H), 4.74 (s, 1H), 4.46 (dd, J ¼ 11.0,
4.9 Hz, 1H), 3.74 (d, J ¼ 10.9 Hz, 1H), 3.24
(d, J ¼ 10.9 Hz, 1H), 2.35–2.25 (m, 1H),
2.03 (s, 3H), 2.00–1.83 (m, 3H), 1.73–1.60
(m, 6H), 1.42 (s, 3H), 1.38 (s, 3H), 1.34–
1.20 (m, 5H), 1.13–1.02 (m, 3H), 0.99 (s,
3H), 0.97 (s, 3H), 0.84 (s, 3H), 0.83 (s, 6H),
0.77 (d, J ¼ 10.3 Hz, 1H); 13C NMR
(100 MHz, CDCl3) d 171.1, 162.7 (d,
JCF ¼ 245.8 Hz), 149.5, 147.2, 127. 5 £ 2
(d, JCF ¼ 8.0 Hz), 126.8 (d, JCF ¼ 3.2 Hz),
119.8, 115.7 £ 2 (d, JCF ¼ 21.6 Hz), 112.0,
80.9, 60.1, 55.3, 55.0, 50.2, 50.1, 47.8, 43.6,
42.7, 40.9, 38.4, 37.8, 37.1, 37.0, 34.2, 33.7,
30.3, 29.2, 27.9, 27.1, 26.9, 23.7, 21.3, 20.9,
18.2, 16.5, 16.2, 16.0, 14.7. HRMS (EI-
TOF): m/z 645.4307 [M þ 1]þ (calcd for
C40H56FN3O3, 645.4306).
3.3.4 Compound 4d: 3-O-acetyl-30-(4-
cyclopropyl-1H-1,2,3-triazol-1-yl) betulin
White solid, m.p. 137–1398C (uncor-
rected); 1H NMR (400 MHz, CDCl3) d
7.18 (s, 1H), 5.00 (s, 1H), 4.85 (q,
J ¼ 15.4 Hz, 2H), 4.67 (s, 1H), 4.46 (dd,
J ¼ 10.5, 5.3 Hz, 1H), 3.73 (d,
J ¼ 10.8 Hz, 1H), 3.23 (d, J ¼ 10.8 Hz,
1H), 2.29–2.23 (m, 1H), 2.04 (s, 3H),
1.98–1.82 (m, 4H), 1.72–1.50 (m, 7H),
1.48–1.31 (m, 5H), 1.30–1.14 (m, 5H),
1.10–1.01 (m, 3H), 0.99 (s, 3H), 0.96 (s,
1H), 0.95 (s, 3H), 0.94–0.89 (m, 2H), 0.83
(s, 6H), 0.81 (s, 3H), 0.80–0.74 (m, 2H);
13C NMR (100 MHz, CDCl3) d 171.1,
150.6, 149.6, 119.9, 111.8, 80.9, 60.0,
55.3, 54.8, 50.2, 50.0, 47.8, 43.6, 42.7,
40.9, 38.4, 37.8, 37.1, 37.1, 34.2, 33.7,
31.6, 29.2, 27.9, 26.9, 23.7, 21.3, 20.9,
18.2, 17.1, 16.5, 16.2, 16.0, 14.7, 7.8 £ 2,
6.7. HRMS (EI-TOF): m/z 591.4407
[M þ 1]þ (calcd for C37H57N3O3,
591.4400).
3.3.3 Compound 4c: 3-O-acetyl-30-(4-
(thiophen-2-yl)-1H-1,2,3-triazol-1-yl)
White solid, m.p. 140–143oC (uncor-
rected); 1H NMR (400 MHz, CDCl3) d
7.65 (s, 1H), 7.37 (d, J ¼ 3.3 Hz, 1H), 7.29
(d, J ¼ 5.0 Hz, 1H), 7.10–7.04 (m, 1H),
5.06 (s, 1H), 4.95 (q, J ¼ 15.4 Hz, 2H),
4.75 (s, 1H), 4.46 (dd, J ¼ 10.8, 5.0 Hz,
1H), 3.74 (d, J ¼ 10.7 Hz, 1H), 3.24 (d,
J ¼ 10.7 Hz, 1H), 2.32–2.21 (m, 1H), 2.04
(s, 3H), 2.00–1.83 (m, 3H), 1.74–1.59 (m,
7H), 1.50–1.34 (m, 5H), 1.33–1.16 (m,
6H), 1.15–1.04 (m, 3H), 0.99 (s, 3H), 0.96
(s, 3H), 0.95–0.88 (m, 1H), 0.8 (s, 3H),
0.83–0.78 (m, 6H), 0.75 (d, J ¼ 3.7 Hz,
1H); 13C NMR (125 MHz, CDCl3) d 171.1,
149.4, 143.0, 132.9, 127.6, 125.1, 124.2,
119.6, 112.1, 80.9, 59.9, 55.3, 55.0, 50.2,
50.1, 47.8, 43.7, 42.7, 40.9, 38.4, 37.8,
37.1, 37.0, 34.1, 33.8, 31.6, 29.2, 27.9,
27.1, 26.9, 23.66, 21.3, 20.9, 18.2, 16.5,
16.2, 15.8, 14.7. HRMS (EI-TOF): m/z
3.3.5 Compound 4e: 3-O-acetyl-30-(4-
butyl-1H-1,2,3-triazol-1-yl) betulin
White solid, m.p. 133–1358C (uncor-
rected); 1H NMR (500 MHz, CDCl3) d
7.23 (s, 1H), 4.98 (s, 1H), 4.85 (q,
J ¼ 15.3 Hz, 2H), 4.65 (s, 1H), 4.43 (dd,
J ¼ 10.7, 5.3 Hz, 1H), 4.08 (q,
J ¼ 10.7 Hz, 1H), 3.70 (d, J ¼ 10.9 Hz,
1H), 3.20 (d, J ¼ 10.9 Hz, 1H), 2.67 (t,
J ¼ 7.5 Hz, 2H), 2.25–2.16 (m, 1H), 2.02
(s, 1H), 2.00 (s, 3H), 1.93–1.85 (m, 2H),
1.68–1.56 (m, 7H), 1.54–1.41 (m, 2H),
1.40–1.32 (m, 6H), 1.25–1.18 (m, 4H),
1.17–1.09 (m, 2H), 1.04–1.00 (m, 2H),
0.96 (s, 3H), 0.93 (s, 3H), 0.89 (t,
J ¼ 7.3 Hz, 3H), 0.84–0.80 (m, 6H), 0.80
(s, 3H), 0.77–0.73 (m, 1H); 13C NMR
(125 MHz, CDCl3) d 171.2, 171.1, 171.1,
149.7, 148.7, 121.1, 111.6, 80.9, 59.9,
55.3, 54.8, 50.2, 49.9, 47.8, 43.5, 42.6,