Novel sulfated oligosaccharide derivatives
一种化合物、通式化合物的技术，应用在新的硫酸化寡糖衍生物领域，能够解决没有表现出抗－IIa活性等问题
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Embodiment 1
[0083] Example 1: 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-tris-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)
[0084] To Trichloroacetate Imidate 1 28 (0.469g, 0.285mmol) in DCM (15mL) was added 1-dodecanol (0.849mmol, 3 equivalents) and MS (50 mg). The mixture was stirred at -20°C for 20 minutes. Add TMSOTf (103μL, 0.57mmol, 2eq) and use Et 3 The mixture was stirred at -20°C for 50 minutes before being quenched with N (38 μL, 0.285 mmol, 1 equivalent). After warming to room temperature, the mixture was filtered and the solids were washed with DCM. The combined filtrate and washing liquid were evaporated on silica gel and passed through column chromatography (silica 2×20cm, CHCl 3 , CHCl 3 -Methanol (99:1 to 98:2 gradient elution) was purified to obtain glycoside 2 in the form of a colorless gum. A two-part fraction BnNHAc (76 mg, 2:Bn...
Embodiment 2
[0089] Example 2: 12-azido-1-dodecanol
[0090] Treat 12-bromo-1 with sodium azide (121 mg, 1.855 mmol, 2 equivalents), tetrabutylammonium iodide (17 mg, 0.0464 mmol, 0.05 equivalents) 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 short column of Celite, and the filter cake was rinsed with ethyl acetate (20 mL). The combined filtrate and washing liquid were evaporated on silica gel, and purified by flash column chromatography (2.5×18cm, hexane-ethyl acetate 6:1, 4:1 to 2:1 gradient elution) to obtain colorless Oily 12-azido-1-dodecanol (193 mg, 92%). 1 H NMR(CDCl 3 , 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).
[0091] 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...
Embodiment 3
[0097] 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)
[0098] Load azide 5 (86mg, 50.3μmol), tert-butanol (100μL, 0.4M), 1-ethynylnaphthalene (83μmol, 2 equivalents), copper sulfate solution (0.3 in water) into a 1mL HPLC sample bottle in the following order M, 14 μL, 4.2 μmol, 10 mol%) and sodium ascorbate solution (1M, in water, 12.4 μL, 12.4 μmol, 30 mol%). The mixture was stirred at room temperature for 11 days. Then the mixture was evaporated on silica gel and flash column chromatography (1×18cm, eluted with a gradient of hexane-ethyl acetate 6:1, 4:1, 2:1, 1:1, 1:2 to 1:3 ) It was purified to obtain a colorless colloid naphthyltriazole 9 (24.2 mg, 26%). 1 H NMR(CDCl 3 , 400MHz) δ 8.38-8.33 (m, 1H), 7.92-7.86 (m, 2H), 7.80 (s, 1H, triaz...
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