Sulfated fuco-galactotetraose and its preparation method and application
A technology for sulfated fucose and lactotetraose, applied to the preparation of sugar derivatives, chemical instruments and methods, esterification of saccharides, etc.
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Embodiment 1
[0052] Example 1 Preparation of p-tolyl 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranoside (2).
[0053] 0°C, L-fucose (1.4g, 7.73mmol) and DMAP (134mg, 1.10mmol) were dissolved in pyridine (30mL), and Ac 2 O (15 mL). The solution was warmed to room temperature and stirred for 12 h, then concentrated to dryness. The residue was dissolved in EtOAc, washed with 5% aqueous citric acid, and washed with saturated NaHCO 3 Washed with aqueous solution and brine. The organic layer was dried over magnesium sulfate, filtered and concentrated to give crude product 1 (2.62g). 0°C, BF 3 ·OEt 2 (1.96mL, 15.47mmol) was added dropwise to crude product 1 and thiocresol (1.15g, 9.28mmol) was dissolved in CH 2 Cl 2 (30mL) solution. After stirring at 0°C for 2 hours, the solution was warmed to room temperature, stirring was continued for 12 hours, and the solution was washed with NaHCO 3 (sat.aq.) to terminate the reaction. The organic phase was washed with 5% NaOH aqueous saturated brine, then dr...
Embodiment 2
[0054] Example 2 Preparation of p-tolyl 2-O-benzyl-3,4-O-isopropylidene-1-thio-β-L-fucopyranoside (3).
[0055] Compound 2 (1.18 g, 2.97 mmol) was dissolved in methanol (20 mL), and MeONa (16 mg, 0.30 mmol) was added. Stir for 12 hours, neutralize with Dowex50WX8 acidic resin, filter, and evaporate to dryness. The residue is dissolved in acetone (20 mL), and 2,2-dimethoxypropane (0.73 mL, 5.932 mmol) and p-toluenesulfonic acid ( 56 mg, 0.30 mmol). Stir at room temperature for 4 hours, add triethylamine (5 mL) to neutralize, and evaporate to dryness. The residue is dissolved in DMF (10 mL), and NaH (60%, 237 mg, 5.93 mmol) is added at 0°C. After 30 min, BnBr (0.71 mL, 5.93 mmol) was added and stirred at room temperature for 5 hours. The mixture was slowly added to water and extracted with ethyl acetate. The organic phase was dried over magnesium sulfate, filtered and evaporated to dryness. Recrystallization from n-hexane gave 3 (1.12 g, 95%). 1 H NMR (400MHz, CDCl 3 )δ7.47–...
Embodiment 3
[0056] Example 3 Preparation of p-tolyl 2-O-benzyl-1-thio-β-L-fucopyranoside (4)
[0057] Compound 3 (1.11g, 2.77mmol) was dissolved in methanol (25mL), and p-toluenesulfonic acid (53mg, 0.28mmol) was added. Stirred at room temperature for 24 hours, neutralized with triethylamine (5mL), and evaporated to dryness. Purification by silica gel column chromatography (ethyl acetate / n-hexane / dichloromethane 1:2:1) gave 4 (895 mg, 90%). 1 H NMR (400MHz, CDCl 3 )δ7.47(d,J=8.1Hz,2H),7.42–7.27(m,5H,ArH),7.12(d,J=7.9Hz,2H),4.96and 4.69(ABq,J=11.0Hz,2H ), 4.53(d, J=9.6Hz, 1H), 3.72(dd, J=5.1, 3.4Hz, 1H), 3.66–3.56(m, 2H), 3.50(t, J=9.3Hz, 1H), 2.48 (d,J=5.3Hz,1H),2.34(s,3H),2.11(d,J=5.3Hz,1H),1.34(d,J=6.5Hz,3H).HRMS(ESI-TOF):m / z Calcd for C 20 h 24 o 4 NaS[M+Na] + :383.1293,Found:383.1294.
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