Molecules 2018, 23, 709
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calcd. for C18H20O6N3F [M + H]+ 394.1. Found: 394.1. HRMS for C18H20O6N3F [M + H]+ 394.1414.
Found: 394.1414.
Furan glucosyl-1,2,3-triazole (5-e). Yield: 84.7%. Oily.1H-NMR (CDCl3):
CCHN), 6.45–6.15 (m, 1H, H-1, and ), 5.28–3.92 (m, 5H, H-2, H-3, H-4, H-5, H-6,
(m, 3H, OMe, and ), 2.15–2.03 (m, 6H, Me2-CO, and δ
); 13C-NMR (CDCl3):
δ
8.27–7.26 (m, 5H, ArH,
and ), 3.53–3.47
169.61, 169.24,
α
β
α
β
α
β
α
β
147.46, 145.81, 136.94, 126.29, 124.38, 122.70, 122.39, 99.82, 93.95, 82.86, 82.31, 81.71, 78.55, 78.00, 76.20,
58.48, 58.33, 50.86, 50.32, 21.26, 20.89, 20.79, 20.53. ESI-MS m/z calcd. for C18H21O8N4 [M + H]+ 421.1.
Found: 421.1. HRMS for C18H21O8N4 [M + H]+ 421.1359. Found: 421.1357.
Furan glucosyl-1,2,3-triazole (5-f). Yield: 82.9%. White solid, m.p. 131.3–133.0 ◦C. 1H-NMR (CDCl3):
δ
7.87–7.27 (m, 5H, ArH, CCHN), 6.45–6.15 (m, 1H, H-1,
α
and
), 2.15–2.04 (m, 6H, Me2-CO,
169.61, 169.56, 169.25, 146.95, 134.02, 129.21, 129.14, 127.12, 121.21, 120.92, 99.82, 94.05,
β
), 5.27–3.90 (m, 5H, H-2, H-3, H-4,
H-5, H-6,
(CDCl3):
α
and
β), 3.52–3.46 (m, 3H, OMe,
α
and
β
α
and
β
); 13C-NMR
δ
82.81, 82.40, 81.81, 78.59, 78.21, 76.18, 58.47, 58.29, 50.53, 50.03, 21.28, 20.92, 20.82, 20.55. ESI-MS m/z
calcd. for C18H21O6N3Cl [M + H]+ 410.1. Found: 410.1. HRMS for C18H21O6N3Cl [M + H]+ 410.1119.
Found: 410.1120.
Furan glucosyl-1,2,3-triazole (F-a). Yield: 90.3%. White solid, m.p. 148.0–149.3 ◦C. 1H-NMR (CDCl3):
7.70–7.21 (m, 11H, ArH, CCHN), 6.40–6.10 (m, 1H, H-1, and ), 5.25–4.00 (m, 7H, H-2, H-3, H-4, H-5,
H-6, Ar-CH2, and 169.50, 169.16, 147.71, 136.93,
), 2.04–1.93 (m, 6H, Me2-CO); 13C-NMR (CDCl3):
δ
α
β
α
β
δ
136.73, 130.54, 128.77, 128.67, 128.61, 128.33, 128.24, 128.10, 128.01, 127.98, 125.72, 121.16, 120.89, 99.70,
94.03, 81.67, 80.12, 80.05, 78.92, 78.12, 76.48, 72.43, 72.18, 50.35, 49.86, 21.13, 20.78, 20.69, 20.42. ESI-MS
m/z calcd. for C24H26O6N3 [M + H]+ 452.1. Found: 452.1. HRMS for C24H26O6N3 [M + H]+ 452.1822.
Found: 452.1821.
Furan glucosyl-1,2,3-triazole (6-b). Yield: 91.6%. White solid, m.p. 110.7–112.5 ◦C. 1H-NMR (CDCl3):
7.67–6.95 (m, 10H, ArH, CCHN), 6.35–6.06 (m, 1H, H-1, and ), 5.20–3.96 (m, 7H, H-2, H-3, H-4, H-5,
H-6, Ar-CH2, and ) 2.22 (s, 3H, Ar-CH3), 1.97–1.86 (m, 6H, Me2-CO, and
); 13C-NMR (CDCl3):
δ
α
β
α
β
α
β
δ
169.25, 168.90, 147.43, 138.12, 136.84, 136.65, 130.28, 128.58, 128.44, 128.38, 128.33, 128.00, 127.92, 127.75,
127.70, 126.08, 122.58, 120.98, 120.68, 99.40, 93.72, 81.43, 79.97, 79.79, 78.70, 76.84, 76.30, 72.16, 71.91,
50.09, 49.58, 21.13, 20.84, 20.49, 20.40, 20.14. ESI-MS m/z calcd. for C25H28O6N3 [M + H]+ 466.1. Found:
466.1. HRMS for C25H28O6N3 [M + H]+ 466.1978. Found: 466.1980.
Furan glucosyl-1,2,3-triazole (6-c). Yield: 92.5%. Yellow solid, m.p. 140.6–141.9 ◦C. 1H-NMR (CDCl3):
7.89–6.85 (m, 10H, ArH, CCHN), 6.49–6.19 (m, 1H, H-1, and ), 5.24–4.03 (m, 7H, H-2, H-3, H-4, H-5,
H-6, Ar-CH2, and ), 3.83 (s, 3H, Ar-CH3), 2.11–2.04 (m, 6H, Me2-CO, and
); 13C-NMR (CDCl3):
δ
α
β
α
β
α
β
δ
170.24, 169.87, 159.71, 159.66, 147.61, 147.55, 137.09, 137.06, 128.78, 128.72, 128.69, 128.31, 128.28, 128.06,
127.11, 123.51, 120.28, 120.12, 114.32, 114.29, 108.00, 100.77, 94.18, 80.80, 80.40, 80.34, 79.89, 78.62, 75.68,
72.51, 72.28, 55.40, 50.33, 49.90, 20.92, 20.81, 20.74, 20.54. ESI-MS m/z calcd. for C25H28O7N3 [M + H]+
482.1. Found: 482.1. HRMS for C25H28O7N3 [M + H]+ 482.1927. Found: 482.1927.
Furan glucosyl-1,2,3-triazole (6-d). Yield: 87.1%. White solid, m.p. 123.8–124.9 ◦C. 1H-NMR (CDCl3):
δ
7.68–6.98 (m, 10H, ArH, CCHN), 6.41–6.11 (m, 1H, H-1,
α
and
β
), 5.26–4.01 (m, 7H, H-2, H-3, H-4,
H-5, H-6, Ar-CH2, and δ
α
β
), 2.06–1.95 (m, 6H, Me2-CO); 13C-NMR (CDCl3):
169.66, 169.58, 169.49,
169.24, 163.93, 161.47, 146.96, 146.94, 136.94, 136.74, 128.75, 128.70, 128.43, 128.34, 128.08, 128.06, 127.57,
127.48, 120.97, 120.71, 115.91, 115.69, 99.77, 94.08, 81.74, 80.15, 80.08, 78.96, 78.16, 76.53, 72.51, 72.24,
50.51, 50.02, 21.20, 20.85, 20.77, 20.49. ESI-MS m/z calcd. for C24H25O6N3F [M + H]+ 470.1. Found:
470.1. HRMS for C24H25O6N3F [M + H]+: 470.1727. Found: 470.1736.
1
Furan glucosyl-1,2,3-triazole (6-e). Yield: 89.4%. Oily. H-NMR (CDCl3):
δ
8.18–7.26 (m, 10H, ArH,
and
169.61, 169.25, 147.36, 145.63, 136.89, 136.86,
136.69, 128.79, 128.73, 128.49, 128.40, 128.09, 128.07, 126.22, 126.20, 124.28, 122.82, 122.53, 99.78, 93.98,
CCHN), 6.42–6.12 (m, 1H, H-1,
α and β), 5.28–4.06 (m, 7H, H-2, H-3, H-4, H-5, H-6, Ar-CH2, α
β
) 2.07–1.96 (m, 6H, Me2-CO); 13C-NMR (CDCl3):
δ