B. K. Singh et al. / Carbohydrate Research 343 (2008) 1153–1162
1159
OCH2Ph), 5.93 (d, 1H, J = 3.7 Hz, H-1), 7.33–7.36 (m,
4.11. 4-Benzyl-1-(3-O-benzyl-5-deoxy-1,2-O-isopropyl-
idene-a-D-xylofuranos-5-yl)-1H-1,2,3-triazole (17)
5H, ArH), 7.53 (s, 1H, triazolyl H); 13C NMR
(75 MHz, CDCl3): d 24.9 (CMe2), 25.5 (CMe2), 47.7
(C-5), 54.8 (CH2OH), 70.7 (OCH2Ph), 77.5 (C-2), 80.3
(C-3), 80.7 (C-4), 103.8 (C-1), 110.7 (CMe2), 121.4
(C-5 triazole), 126.6 (Ar), 127.0 (Ar), 127.3 (Ar), 135.5
(Ar), 146.6 (C-4 triazole); ESIMS: 362.3 (M+H)+;
HRMS: calcd for C18H24N3O5 (M+H)+: 362.1716;
found: 362.1714.
Compound 17 was obtained by the reaction of 12 (0.3 g,
1 mmol) and 3-phenyl-1-propyne (0.13 mL, 1 mmol) as
a white solid: 0.41 g, 91%; mp 81–82 °C; [a]D À86 (c
0.1, CHCl3); IR (neat) cmÀ1: 2925, 2361, 1647, 752;
1H NMR (200 MHz, CDCl3 + CCl4): d 1.28 (s, 3H,
CH3 of CMe2), 1.41 (s, 3H, CH3 of CMe2), 3.90 (d,
1H, J = 2.5 Hz, H-3), 4.03 (d, 2H, J = 4.2 Hz, CH2Ph),
4.37–4.61 (m, 6H, H-4, H-5, H-2, OCH2Ph), 5.90 (d, 1H,
J = 3.7 Hz, H-1), 7.17–7.34 (m, 11H, ArH, triazolyl H);
13C NMR (50 MHz, CDCl3 + CCl4): d 26.6 (CMe2),
27.2 (CMe2), 32.6 (CH2Ph), 49.2 (C-5), 72.4 (OCH2Ph),
79.2 (C-2), 82.0 (C-3), 82.3 (C-4), 105.5 (C-1), 112.4
(CMe2), 122.8 (C-5 triazole), 126.8 (Ar), 128.2 (Ar),
128.6 (Ar), 128.9 (Ar), 129.0 (Ar), 129.1 (Ar), 137.2
(Ar), 139.5 (Ar), 147.7 (C-4 triazole); ESIMS: 422.3
(M+H)+; HRMS: calcd for C24H27N3O4 (M)+:
421.2002; found: 421.2008.
4.9. 1-(3-O-Benzyl-5-deoxy-1,2-O-isopropylidene-a-D-
xylofuranos-5-yl)-4-n-hexyl-1H-1,2,3-triazole (15)
Compound 15 was obtained by the reaction of 12
(0.7 g, 2.3 mmol) with 1-octyne (0.4 mL, 2.3 mmol)
as a colourless solid: 0.79 g, 82%; mp 68–69 °C; [a]D
À63 (c 0.1, CHCl3); IR (KBr) cmÀ1: 3068, 2926,
1
1458; H NMR (200 MHz, CDCl3 + CCl4): d 0.88 (t,
3H, J = 6.6 Hz, CH3), 1.29–1.38 (m, 9H, 3 Â CH2,
CH3 of CMe2), 1.41 (s, 3H, CH3 of CMe2) 1.61–
1.64 (m, 2H, CH2), 2.66 (t, 2H, J = 7.6 Hz, CH2),
3.94 (d, 1H, J = 2.2 Hz, H-3), 4.43–4.57 (m, 3H, H-
4, H-5), 4.62–4.75 (m, 3H, H-2, OCH2Ph), 5.93 (d,
1H, J = 3.7 Hz, H-1), 7.27–7.33 (m, 6H, ArH, triazol-
yl H); 13C NMR (50 MHz, CDCl3 + CCl4): d 14.5
(CH3), 22.9 (CH2), 26.0 (CH2), 26.6 (CMe2), 27.1
(CMe2), 29.3 (CH2), 29.7 (CH2), 31.9 (CH2), 49.2
(C-5), 72.3 (OCH2Ph), 79.3 (C-2), 82.0 (C-3), 82.3
(C-4), 105.5 (C-1), 112.3 (CMe2), 121.8 (C-5 triazole),
128.2 (Ar), 128.6 (Ar), 129.0 (Ar), 137.2 (Ar), 148.6
(C-4 triazole); ESIMS: 416.4 (M+H)+; Anal. Calcd
for C23H33N3O4 C, 66.48; H, 8.00; N, 10.11. Found:
C, 66.39; H, 8.11; N, 10.16.
4.12. 1-(Methyl 5-deoxy-2,3-O-isopropylidene-b-D-ribo-
furanosid-5-yl)-4-phenyl-1H-1,2,3-triazole (20)
Compound 20 was obtained by the reaction of 19 (0.5 g,
2.2 mmol) and phenylacetylene (0.24 mL, 2.20 mmol) as
a colourless solid: 0.54 g, 70%; mp 134–135 °C, lit.16 mp
135–136 °C; [a]D À34 (c 0.1, CHCl3); IR (KBr) cmÀ1
:
1
3086, 2944, 1655; H NMR (200 MHz, CDCl3 + CCl4):
d 1.30 (s, 3H, CH3 of CMe2), 1.45 (s, 3H, CH3 of CMe2),
3.41 (s, 3H, OCH3), 4.44–4.63 (m, 3H, H-4, H-5), 4.65
(d, 1H, J = 5.9 Hz, H-3), 4.75 (d, 1H, J = 5.9 Hz,
H-2), 5.01 (s, 1H, H-1), 7.31–7.44 (m, 3H, ArH), 7.80–
7.85 (m, 3H, ArH, triazolyl H); 13C NMR (50 MHz,
CDCl3 + CCl4): d 25.3 (CMe2), 26.8 (CMe2), 53.4
(C-5), 55.9 (OCH3), 82.1 (C-2), 85.3(C-3), 85.5 (C-4),
110.4 (C-1), 113.2 (CMe2), 120.0 (C-5 triazole), 126.1
(Ar), 128.5 (Ar), 129.1 (Ar), 130.9 (Ar), 148.3 (C-4 tri-
azole); ESIMS: 332 (M+H)+; HRMS: calcd for
C16H18N3O4 (MÀCH3)+: 316.1297; found: 316.1295.
4.10. 1-(3-O-Benzyl-5-deoxy-1,2-O-isopropylidene-a-D-
xylofuranos-5-yl)-4-n-pentyl-1H-1,2,3-triazole (16)
Compound 16 was obtained by the reaction of 12 (0.3 g,
1.1 mmol) and 1-heptyne (0.14 mL, 1.1 mmol) as an oil:
0.38 g, 90%; [a]D À78 (c 0.1, CHCl3); IR (neat) cmÀ1
:
2930, 2364, 1457, 1217; 1H NMR (200 MHz,
CDCl3 + CCl4): d 0.89 (t, 3H, J = 6.3 Hz, CH3), 1.25–
1.36 (m, 7H, 2 Â CH2, CH3 of CMe2). 1.42 (s, 3H,
CH3 of CMe2), 1.61–1.69 (m, 2H, CH2), 2.66 (t, 2H,
J = 8.0 Hz, CH2), 3.95 (d, 1H, J = 2.6 Hz, H-3), 4.43–
4.51 (m, 3H, H-4, H-5), 4.57–4.75 (m, 3H, H-2,
OCH2Ph), 5.93 (d, 1H, J = 3.7 Hz, H-1), 7.27–7.38 (m,
6H, ArH, triazolyl H); 13C NMR (50 MHz,
CDCl3 + CCl4): d 14.4 (CH3), 22.8 (CH2), 26.0 (CH2),
26.6 (CMe2), 27.1 (CMe2), 29.4 (CH2), 31.8 (CH2),
49.2 (C-5), 72.4 (OCH2Ph), 79.3 (C-2), 82.0 (C-3), 82.3
(C-4), 105.5 (C-1), 112.3 (CMe2), 121.9 (C-5 triazole),
128.2 (Ar), 128.6 (Ar), 129.0 (Ar), 137.2 (Ar),
148.6 (C-4 triazole); ESIMS: 402.3 (M+H)+; HRMS:
calcd for C22H30N3O4 (MÀH)+: 400.2236; found:
400.2226.
4.13. 4-Hydroxymethyl-1-(methyl 5-deoxy-2,3-O-isopro-
pylidene-b-D-ribofuranosid-5-yl)-1H-1,2,3-triazole (21)
Compound 21 was obtained by the reaction of 19
(3.70 g, 16.2 mmol) and propargyl alcohol (1.10 mL,
16.2 mmol) as a brown solid: 4 g, 87%; [a]D À36 (c 0.1,
CHCl3); mp 81–82 °C; IR (KBr) cmÀ1: 3462, 2985,
1
1653; H NMR (200 MHz, CDCl3): d 1.30 (s, 3H, CH3
of CMe2), 1.45 (s, 3H, CH3 of CMe2), 3.38 (s, 3H,
OCH3), 4.40–4.59 (m, 5H, H-4, H-5, CH2OH), 4.65 (d,
1H, J = 5.9 Hz, H-3), 4.74 (d, 1H, J = 6.2 Hz, H-2),
5.01 (s, 1H, H-1), 7.68 (s, 1H, triazolyl H); 13C NMR
(50 MHz, CDCl3): d 25.3 (CMe2), 26.7 (CMe2), 53.5
(C-5), 55.9 (OCH3), 56.6 (CH2OH), 82.1 (C-2), 85.3
(C-3), 85.5 (C-4), 110.4 (C-1), 113.3 (CMe2), 122.5