Novel sulfated oligosaccharide derivatives
A compound, the technology of the general formula compound, applied in the field of new sulfated oligosaccharide derivatives, can solve the problems such as not showing anti-IIa activity
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Embodiment 1
[0082] Example 1: Dodecyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1→3)-2,4,6-tri-O-acetyl Base-α-D-mannopyranosyl-(1→3)-2,4,6-tri-O-acetyl-α-D-mannopyranosyl-(1→3)-2,4 , 6-tri-O-acetyl-α-D-mannopyranosyl-(1→2)-3,4,6-tri-O-acetyl-α-D-mannopyranoside (2)
[0083] trichloroacetate imidate 1 28 (0.469g, 0.285mmol) in DCM (15mL) was added 1-dodecanol (0.849mmol, 3 equiv) and MS (50 mg). The mixture was stirred at -20°C for 20 minutes. TMSOTf (103 μL, 0.57 mmol, 2 equiv) was added and washed with Et 3 The mixture was stirred at -20°C for 50 minutes before being quenched with N (38 μL, 0.285 mmol, 1 equiv). After warming to room temperature, the mixture was filtered and the solids were rinsed with DCM. The combined filtrate and washings were evaporated on silica gel and purified by column chromatography (silica 2 x 20 cm, CHCl 3 , CHCl 3 -methanol 99:1 to 98:2 gradient elution) to obtain glycoside 2 as a colorless gum. Two fractions of BnNHAc (76 mg, 2:BnNHAc=5:3; 179 mg...
Embodiment 2
[0088] Example 2: 12-Azido-1-dodecanol
[0089] 12-Bromo-1 was treated with sodium azide (121 mg, 1.855 mmol, 2 equiv), tetrabutylammonium iodide (17 mg, 0.0464 mmol, 0.05 equiv) and saturated aqueous sodium bicarbonate (0.9 mL) in the following order - A mixture of dodecanol (246 mg, 0.927 mmol) in tert-butanol (1.8 mL, 0.5M). The mixture was stirred at room temperature for 4 days. The mixture was filtered through a plug of Celite and the filter cake was rinsed with ethyl acetate (20 mL). The combined filtrate and washings were evaporated on silica gel and purified by flash column chromatography (2.5 x 18 cm, gradient elution with hexane-ethyl acetate 6:1, 4:1 to 2:1) to give colorless 12-Azido-1-dodecanol (193 mg, 92%) as an oil. 1 H NMR (CDCl3 , 400MHz): 3.62(t, 2H, J=7.0, OCH 2 ), 3.24(t, 2H, J=7.0, NCH 2 ), 1.61-1.51(m, 4H), 1.35-1.25(m, 16H).
[0090] 12-Azidododecyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1→3)-2,4,6-tri-O- Acetyl-α-D-mannopyranosyl-(1→3)-2,4,6...
Embodiment 3
[0096] Example 3: 12-(4-Naphthyl-1-yl-[1,2,3]triazol-1-yl)dodecyl 2,3,4,6-tetra-O-acetyl-α -D-mannopyranosyl-(1→3)-2,4,6-tri-O-acetyl-α-D-mannopyranosyl-(1→3)-2,4,6- Tri-O-acetyl-α-D-mannopyranosyl-(1→3)-2,4,6-tri-O-acetyl-α-D-mannopyranosyl-(1→2 )-3,4,6-tri-O-acetyl-α-D-mannopyranoside (9)
[0097] Azide 5 (86 mg, 50.3 μmol), tert-butanol (100 μL, 0.4 M), 1-ethynylnaphthalene (83 μmol, 2 equiv), copper sulfate solution (0.3 M, 14 μL, 4.2 μmol, 10 mol%) and sodium ascorbate solution (1 M in water, 12.4 μL, 12.4 μmol, 30 mol%). The mixture was stirred at room temperature for 11 days. The mixture was then evaporated on silica gel and flash column chromatography (1×18 cm, gradient elution with hexane-ethyl acetate 6:1, 4:1, 2:1, 1:1, 1:2 to 1:3 ) to give naphthyltriazole 9 (24.2 mg, 26%) as a colorless gum. 1 H NMR (CDCl 3 , 400MHz) δ8.38-8.33 (m, 1H), 7.92-7.86 (m, 2H), 7.80 (s, 1H, triazole-CH), 7.72 (dd, 1H, J=7.3, 1.5), 7.54- 7.48(m, 3H), 5.31-5.15(m, 8H), 5.03-4.87(m,...
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