Method for preparing voglibose and corresponding intermediate
A technology of voglibose and intermediates, which is applied in the field of voglibose preparation, and can solve the problems of easy leakage during operation, environmental pollution, and high bromine specificity
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[0096] The present invention also provides a synthetic method of the intermediate (as shown in formula II), comprising the steps of:
[0097]
[0098] Said intermediates are obtained by reacting a compound of formula I with a peroxide.
[0099] Preferably, the peroxide is selected from hydrogen peroxide, m-chloroperoxybenzoic acid, or other peroxyacids such as peracetic acid, etc.;
[0100] Preferably, the reaction is carried out in a first solvent, and the first solvent used is a solvent capable of dissolving the compound of formula I and does not react with the peroxide; more preferably, the first solvent used is selected from halogenated hydrocarbon solvents Such as dichloromethane, chloroform, 1,2-dichloroethane, etc.
[0101] Preferably, the molar ratio of the compound of formula I to the peroxide is 1:1-1:4.
[0102] Preferably, the reaction temperature is 40°C-80°C. The reaction time is 5-20 hours.
[0103] The method for synthesizing Jinggang mycosamine or vogli...
Embodiment 1
[0135] Preparation of intermediates as shown in formula II: R 1 is benzyl, R 2 for acetyl,
[0136] Formula I compound (32.8g) is dissolved in 750ml chloroform, adds 33.3g anhydrous Na 2 HPO 4 , another m-chloroperoxybenzoic acid (19.4g, 85%) was dissolved in chloroform (400ml), and then the chloroform solution of m-chlorobenzoic acid was added dropwise to the chloroform solution of intermediate I at 20°C-25°C, 30 After dripping in minutes, heat up to reflux, reflux for 6-8 hours, the reaction is complete, stop stirring, cool to room temperature, then stir at 0°C for 2 hours, filter, wash the insoluble matter with chloroform, and then wash with 20% sulfur Washed with sodium sulfate, then washed with saturated sodium bicarbonate, then washed with saturated brine, dried over anhydrous magnesium sulfate, concentrated, the residue was passed through a silica gel column, washed with toluene: ethyl acetate (2:1) to obtain the product 30.7 g, yield 90.4%.
Embodiment 2
[0138] Preparation of intermediates as shown in formula II: R 1 is benzyl, R 2 tert-butyldimethylsilyl
[0139] Formula I compound (24.8g) is dissolved in 350ml chloroform, adds 17.0g anhydrous Na 2 HPO 4 , and another m-chloroperoxybenzoic acid (10.0g, 85%) was dissolved in chloroform (200ml), and then the chloroform solution of m-chlorobenzoic acid was added dropwise to the chloroform solution of the compound of formula I at 20°C-25°C, 30 After dripping in minutes, heat up to reflux, reflux for 6-8 hours, the reaction is complete, stop stirring, cool to room temperature, then stir at 0°C for 2 hours, filter, wash the insoluble matter with chloroform, and then wash with 20% sulfur Washed with sodium sulfate, then washed with saturated sodium bicarbonate, then washed with saturated brine, dried over anhydrous magnesium sulfate, concentrated, the residue was passed through a silica gel column (500ml), the product was collected, concentrated and dried to obtain 23.4g of a col...
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