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3-benzyloxy-tetrahydropyrane, preparation method thereof and preparation method of single-configured tetrahydropyrane-3-cyclitol

A technology of tetrahydropyran and benzyloxy, applied in the field of medicine, can solve the problems of difficult preparation and high cost of tetrahydropyran-3-cycloalcohol, and achieve the effects of being suitable for large-scale production, low cost and simple synthesis method

Active Publication Date: 2017-10-17
浙江药领医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The third object of the present invention is to provide a method for preparing tetrahydropyran-3-cyclol with a single configuration, so as to solve the difficulty in preparing and costing the tetrahydropyran-3-cyclol with a single configuration in the prior art. high technical issues

Method used

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  • 3-benzyloxy-tetrahydropyrane, preparation method thereof and preparation method of single-configured tetrahydropyrane-3-cyclitol
  • 3-benzyloxy-tetrahydropyrane, preparation method thereof and preparation method of single-configured tetrahydropyrane-3-cyclitol
  • 3-benzyloxy-tetrahydropyrane, preparation method thereof and preparation method of single-configured tetrahydropyrane-3-cyclitol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Synthesis of S-2-benzyloxy-pentane-1,5-diol:

[0048]

[0049] Dissolve 60g (0.41mol) of L-glutamic acid in 120ml of concentrated hydrochloric acid, add 60ml of water, cool down to -5°C, add sodium nitrite solution dropwise at this temperature, and the sodium nitrite solution is 42g (0.62mol) Dissolve sodium nitrite in 40ml of water, raise the sodium nitrite solution dropwise to room temperature, react for 18 hours, and concentrate the reaction solution under reduced pressure after the reaction, the temperature is lower than 50°C, the residue is washed with ethyl acetate, Combine the organic phases, dry them with anhydrous sodium sulfate, concentrate again under reduced pressure, and directly add them to 300ml of anhydrous methanol, add 0.3ml of concentrated hydrochloric acid, heat and reflux for 24h, cool down to room temperature after the reaction, add 600ml of ethyl acetate, and use saturated Wash twice with 200ml of sodium bicarbonate, wash three times with satur...

Embodiment 2

[0052] Synthesis of (S)-3-benzyloxy-tetrahydropyran:

[0053]

[0054] Dissolve 21g (0.1mol) of S-2-benzyloxy-pentane-1,5-diol synthesized in Example 1 in 400ml of the first organic solvent, dichloromethane, and add the organic base Et 3 N 30.3g (0.3mol), 4-dimethylaminopyridine 0.1mol, slowly drop the dichloromethane solution of trifluoromethanesulfonic anhydride, the temperature is controlled at 20°C, the dichloromethane solution of trifluoromethanesulfonic anhydride is 28.2 g, that is, 0.1 mol of trifluoromethanesulfonic anhydride is dissolved in 400 ml of the second organic solvent methylene chloride and obtained. After the dropwise addition, keep the temperature for reaction for 20 minutes, add 25.2 g (0.3 mol) of solid sodium bicarbonate, and stir After 30 minutes, filter and concentrate, add 200ml of the third organic solvent petroleum ether, wash with saturated chlorinated solution, dry over sodium sulfate, concentrate and pass through the column, and carry out grad...

Embodiment 3

[0056] Synthesis of tetrahydropyran-3(S)-cycloalcohol:

[0057]

[0058] Dissolve 6.3g (30mmol) of the compound shown in Formula I obtained in Example 2 in 60ml of the fourth organic solvent, anhydrous methanol, and add 630mg of Pd(OH) 2 After the system is decompressed and evacuated with a vacuum water pump, hydrogen gas is introduced, and the steps of decompression and hydrogen gas introduction are repeated three times, keeping the hydrogen pressure at 0.5 atmospheres, raising the temperature to 40°C for 18 hours, and filtering with diatomaceous earth after the reaction , the filtrate is concentrated and passed through the column. When passing through the column, petroleum ether and ethyl acetate are used as eluents for gradient elution, wherein the volume ratio of petroleum ether and ethyl acetate varies from 50:1 to 3:1. 2.5 g (24.5 mmol) of compound 1 was a colorless oil, and the yield was 82%. -6.0(c 1.1, EtOH), 1 H NMR (400MHz, CDCl 3 ,ppm): δ=3.79-3.73(m,2H),3.6...

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Abstract

The invention relates to 3-benzyloxy-tetrahydropyrane, a preparation method thereof and a preparation method of single-configured tetrahydropyrane-3-cyclitol, and belongs to the technical field of medicines. The 3-benzyloxy-tetrahydropyrane has a structure as shown in a formula I or formula II. Etherification and one-step ring-closure reaction are performed on single-configured 2-benzyloxy-pentane-1, 5-diol through anhydride catalysis molecules to generate the 3-benzyloxy-tetrahydropyrane, the 3-benzyloxy-tetrahydropyrane can be used for preparing the single-configured tetrahydropyrane-3-cyclitol, and the preparation method is simple, low in cost and suitable for mass production.

Description

technical field [0001] The invention relates to 3-benzyloxy-tetrahydropyran, a preparation method thereof, and a preparation method of single-configuration tetrahydropyran-3-cyclanol, belonging to the technical field of medicine. Background technique [0002] Tetrahydropyran-3-cyclol is an important pharmaceutical intermediate with important uses, for example, it can be used to synthesize Mnk1 and Mnk2 kinase inhibitors, inhibit human lung adenocarcinoma cell proliferation and induce its apoptosis; it can also It is used for the synthesis of glucokinase inhibitors to treat diabetes; it can also be used for the synthesis of ATR kinase inhibitors and is used in the field of tumor treatment; tetrahydropyran-3-cyclol has important application prospects and commercial value. [0003] The synthesis of racemic tetrahydropyran-3-cycloalcohol is relatively simple, and there have been many reports in the literature. For example, 3,4-dihydropyran can be used as a raw material, and che...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D309/12
CPCC07B2200/07C07D309/12
Inventor 吴豫生耿阳邹大鹏牛成山李敬亚郑茂林梁阿朋
Owner 浙江药领医药科技有限公司
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