Fondaparinux sodium and its intermediate, and preparation method
A technology for fondaparinux sodium and intermediates, which is applied in the field of chemical preparation, can solve the problems of difficult to make high purity fondaparinux sodium, difficult to make high product purity, high production cost, etc., and reduce the difficulty of purification and production costs , Reduce the difficulty of synthesis and reduce the production cost
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[0057] 2. The preparation route of disaccharide (BA-2) ;
[0058] Step 1, in the presence of a catalyst, monosaccharide B-1 and monosaccharide A-1 are coupled to obtain disaccharide BA-1; Step 2, in the presence of an organic solvent and an organic base, disaccharide BA-1 Deprotection with thiourea gives the disaccharide BA-2. The synthetic route is as follows:
[0059]
[0060] 3. Preparation route of tetrasaccharide (DCBA-2) ;
[0061] Step 1, in the presence of an organic solvent and a catalyst, the disaccharide BA-2 and the disaccharide DC-3 are coupled to obtain the tetrasaccharide DCBA-1; Step 2, in the presence of an organic solvent and an organic base, the tetrasaccharide DCBA-1 -1 was deprotected with thiourea to give the tetrasaccharide DCBA-2. The synthetic route is as follows:
[0062]
[0063] 4. Preparation route of pentasaccharide (EDCBA-1) ;
[0064] In the presence of organic solvents and catalysts, tetrasaccharide DCBA-2 and monosaccharide E-...
Embodiment 1
[0069] The preparation of embodiment 1, disaccharide (BA-2);
[0070] 0.3 kg of compound (A-1) and 0.41 kg of compound (B-1) were dissolved in 4.5 liters of dichloromethane, cooled to 0°C, added with 0.15 kg of silver trifluoromethanesulfonate, and stirred at 0°C for 2-3 hours. After filtration and concentration under reduced pressure, 0.7 kg of disaccharide compound (BA-1) was obtained.
[0071] 0.7 kg of disaccharide compound (BA-1) and 0.07 kg of thiourea were dissolved in 1.2 liters of ethanol and 1.8 liters of pyridine, and the reaction was heated to 70-80°C and stirred for 1 hour. After the reaction was completed, the temperature was lowered to room temperature, followed by post-treatment with water and dichloromethane, and the separated organic phase was successively washed with potassium bisulfate solution, sodium bicarbonate solution and saturated brine, and dried over anhydrous sodium sulfate. After concentration, the crude product was purified by column chromatog...
Embodiment 2
[0076] Embodiment 2, the preparation of disaccharide (BA-2);
[0077] 0.3 kg of compound (A-1) and 0.41 kg of compound (B-1) were dissolved in 4.5 liters of dichloromethane, cooled to -50 ° C, added 0.15 kg of silver trifluoromethanesulfonate, stirred at -50 ° C for 2-3 Hour. After filtration and concentration under reduced pressure, 0.7 kg of disaccharide compound (BA-1) was obtained.
[0078] 0.7 kg of disaccharide compound (BA-1) and 0.07 kg of thiourea were dissolved in 1.2 liters of ethanol and 1.8 liters of pyridine, and the reaction was heated to 60-70°C and stirred for 1 hour. After the reaction was completed, the temperature was lowered to room temperature, followed by post-treatment with water and dichloromethane, and the separated organic phase was successively washed with potassium bisulfate solution, sodium bicarbonate solution and saturated brine, and dried over anhydrous sodium sulfate. After concentration, the crude product was purified by column chromatogr...
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