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Cyclodextrin derivatives and preparation method thereof
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A technology for derivatives and cyclodextrins is applied in the field of β-cyclodextrin derivatives and their preparation, which can solve the problems of poor reaction stereoselectivity and low reaction yields.
Active Publication Date: 2021-11-05
淮北云端文化传媒有限公司
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Problems solved by technology
However, although the catalytic reaction of the above-mentioned β-cyclodextrin achieves high regioselectivity, the reaction stereoselectivity is not good, and it is basically a racemic mixture
In addition, the yield of the reaction is not high
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Embodiment 1
[0042] Under nitrogen protection, 12.5 g of compound 1 (5.21 mmol) was added into 500 mL of anhydrous NMF.
[0043]
[0044] Add 3.50 g NaH (0.145 mol) and stir for 3 hours. To the reaction mixture was added 0.55 g NaI (3.6 mmol), followed by a solution of (R)-β-methyl-γ-butyrolactone (11 g, 109.6 mmol) dissolved in DMF dropwise via syringe. Heated to 75°C and stirred for 48h. Excess NaH was degraded by slow addition of methanol. The solvent was removed by rotary evaporation under reduced pressure, and the obtained brown solid was dried in vacuo. Ultrafiltration through a filter membrane with MWCO=1000, concentrated to give a brown solid, which was dried in vacuo. Washing 3 times with dry acetone afforded Compound 2 (3.6 g, 69%) as an off-white solid. 1 H NMR(600MHz,d6-DMSO):6.9-7.3(7*10H),5.12(d,7*1H),4.94(d,7*1H),4.59(d,7*1H),4.52(d, 7*1H),4.43(d,7*1H),3.72-4.03(m,7*4H),3.2-3.5(m,7*4H),2.13(m,7*2H),1.54(t,7 *1H),1.02(m,7*3H). 13 CNMR(150MHz,d6-DMSO):178.2,138.9,137...
Embodiment 2-1 to 2-5
[0046] Accurately weigh 4.3g of chloroform, 0.025mol of benzaldehyde, cyclodextrin derivative (compound 2) dispersion / solution and quaternary ammonium salt of the formulation amount in Table 1, and put it into a magnetic stirrer, dropping funnel and thermometer In a three-necked flask, mix well. Stir at 50 °C for 15 min. Then, 8 mL of an aqueous solution containing 5 g of sodium hydroxide was added dropwise from the dropping funnel to react, while stirring continuously. After the addition is complete, keep the temperature at 50°C and continue the reaction for 8 hours. After the reaction is completed, add an appropriate amount of water to dissolve the precipitate formed by the reaction. Adjust the pH of the solution to 3 with 1M dilute hydrochloric acid, and then extract 3 times with 20 mL of ether. The extracts were combined, dried with anhydrous sodium sulfate, evaporated to dryness, and the residual precipitate was analyzed by high-performance chromatography, and column ch...
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Abstract
A cyclodextrin derivative and a preparation method thereof are disclosed. The structural formula of the derivative is shown in Formula 2. In addition, the preparation method of the above-mentioned cyclodextrin derivatives is also disclosed, the method comprising: obtaining the compound of formula 1; making the compound of formula 1 react with (R)-β-methyl-γ-butylene in the presence of a base and a solvent ester reaction. The above cyclodextrin derivatives can be used as phase transfer catalysts to catalyze the asymmetric synthesis reaction of mandelic acid, the reaction conditions are mild, the stereoselectivity is strong and the yield is high.
Description
technical field [0001] The invention belongs to the technical field of organic compounds, and relates to a cyclodextrin derivative and a preparation method thereof, in particular to a beta-cyclodextrin derivative and a preparation method thereof. Background technique [0002] Cyclodextrin is a product obtained by degrading amylose under the action of cyclodextrin glucosyltransferase, which is formed by ring-linking multiple D-glucopyranose units, also known as cyclodextrose. It has the characteristics of external hydrophilic and internal hydrophobic. This has led to beta-cyclodextrin being widely used in the fields of enhancing drug stability, increasing solubility, improving bioavailability, reducing toxic and side effects, chiral resolution and composite catalysis. [0003] In the past two or three decades, cyclodextrin, as a simple organic macromolecule, has formed host-guest inclusion complexes with a wide range of substances through intermolecular interactions. The ab...
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