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Intermediates of pregnane saponin P57 and derivatives thereof, preparation method and application of intermediates, and pregnane saponin P57 derivatives

A compound and selected technology, applied in the directions of steroids, chemical instruments and methods, glycoside steroids, etc., can solve the problems of troublesome separation and purification, lack of synthesis of P57, low yield of glycosylation, etc.

Pending Publication Date: 2022-02-22
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI +1
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  • Abstract
  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

The disadvantage of this method is that the starting material is digoxin, a natural extract, and the cost is relatively high, and it needs to be degraded to obtain digoxin aglycon, resulting in a large waste, and the separation and purification are troublesome; Toxic solvent; P57 aglycon Hoodigogenin A and sugar splicing adopt step-by-step glycosylation, and the yields of the two glycosylation are low
The industrialization economics of the whole route are poor
[0008] In summary, there is still a lack of a method suitable for industrialized synthesis of P57 in the art

Method used

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  • Intermediates of pregnane saponin P57 and derivatives thereof, preparation method and application of intermediates, and pregnane saponin P57 derivatives
  • Intermediates of pregnane saponin P57 and derivatives thereof, preparation method and application of intermediates, and pregnane saponin P57 derivatives
  • Intermediates of pregnane saponin P57 and derivatives thereof, preparation method and application of intermediates, and pregnane saponin P57 derivatives

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Experimental program
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Effect test

preparation example Construction

[0069] The preparation method of compound P57

[0070] The steps of the compound P57 preparation method of the present invention are as follows:

[0071]

[0072] Step (1): Construction of the 12-position β hydroxyl group: References (Angew.Chem.Int.Ed.2009, 48, 7911-7914; J.Am.Chem.Soc.2015, 137, 13776-13779.), to Dehydroepiandrosterone (DHEA) is prepared as a raw material through three known reactions (3-hydroxyl protecting group protection, 17-position carbonyl to form enamine, long-range C-H bond activation to form 12-hydroxyl). Among them, R 4 from C 1 -C 6 Alkanoyl, benzoyl or para-substituted benzoyl, three (C 3 -C 9 Alkyl)silyl, three (C 9 -C 16 Aryl) silyl, allyl, benzyl or substituted benzyl on the benzene ring, or hydrogen; the para-substituent of the para-substituted benzoyl is methoxy, nitro, azide Base, halogen; substituted benzyl on the benzene ring refers to naphthylidene, p-methoxyphenyl, p-methylphenyl, p-nitrobenzyl, and p-halogen substituted benz...

Embodiment 1

[0106] The synthesis of embodiment 1 compound 2-4

[0107]

[0108] According to the method of literature (Angew.Chem.Int.Ed.2009,48,7911-7914; J.Am.Chem.Soc.2015,137,13776-13779.), using dehydroepiandrosterone as raw material, after 3 Compound 2-2 was prepared by one-step reaction. Compound 2-2: 1 H NMR (400MHz, CDCl 3)δ7.36-7.24(m,5H),5.37(brs,1H),4.56(s,2H),3.80(dd,J=11.3,4.7Hz,1H),3.31-3.23(m,1H),3.10 (s,1H),2.50-2.43(m,2H),2.31-2.26(m,1H),2.15-2.08(m,2H),2.04-1.94(m,2H),1.89-1.78(m,2H) ,1.68-1.40(m,5H),1.27-1.20(m,1H),1.13-1.00(m,2H),1.03(s,3H),0.95(s,3H); 13 C NMR (100MHz, CDCl 3 )δ141.2, 139.0, 128.4, 127.6, 127.5, 120.7, 78.3, 72.7, 70.0, 51.4, 49.6, 49.2, 39.1, 37.2, 37.2, 35.8, 30.6, 30.5, 28.3, 28.3, 21.7, 19.4, 8.1; 7ESIMS5[ M+Na] + .

[0109] Add Ph to the dry three-neck flask 3 Add THF (200mL) to PEtBr (28.5g, 76.8mmol) and t-BuOK (8.60g, 76.8mmol), and stir at room temperature for 40min to obtain a blood-red turbid liquid. Compound 2-2 (10.1g dissolv...

Embodiment 2

[0111] The synthesis of embodiment 2 compound 2-5

[0112]

[0113] Compound 2-4 (6.70g, 15.8mmol) was dissolved in dry DMF (150mL), imidazole (3.23g, 47.4mmol) and tert-butyldimethylsilyl chloride (3.57g, 23.7mmol) were added, and the reaction was stirred at room temperature 20h. TLC showed that the reaction was complete, diluted with ethyl acetate, washed successively with saturated aqueous sodium bicarbonate and saturated brine, dried over anhydrous sodium sulfate, concentrated, column chromatography (PE / EtOAc=12:1), and a white solid ( 8.2 g, 96%).

[0114] The above white solid (9.20 g, 17.1 mmol) was dissolved in dry CH 2 Cl 2 (5mL), add Dess-Martin oxidant (DMP) (18.1g, 42.7mmol) and NaHCO 3 (5.0g, 59.9mmol), stirred for 2h. TLC showed that the reaction was complete, diluted with EtOAc, followed by saturated Na 2 SO 3 The solution was washed with saturated aqueous sodium bicarbonate and saturated brine, dried over anhydrous sodium sulfate, concentrated, and su...

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Abstract

The invention relates to intermediates, as shown in a formula I, for pregnane saponin P57 and derivatives thereof, a preparation method and application of the intermediates, and the pregnane saponin P57 derivatives. According to the method, synthesis of P57 and derivatives thereof is realized by adopting a convergent synthesis strategy, a synthesis route is short, yield is high, and the method is suitable for industrial production. Each substituent in the formula I is as defined in the specification.

Description

technical field [0001] The present invention relates to the intermediate, preparation method and application of pregnane saponin P57 and derivatives thereof, and pregnane steroside P57 derivatives. Background technique [0002] In 2005, the World Health Organization (WHO) reported that the number of overweight adults worldwide had reached 1.6 billion, of which 400 million were obese. In the same year, a survey of children's health found that more than 20 million children under the age of five were overweight. In addition to the inconvenience of exercise and the imbalance of body proportions, obesity can induce many diseases, such as diabetes, cardiovascular and cerebrovascular diseases, high blood pressure and sleep apnea syndrome. Therefore, obesity is an important public health problem facing mankind in the 21st century, and it is also defined as a disease by the World Health Organization. To deal with obesity, in addition to a reasonable diet, developing good living hab...

Claims

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Application Information

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IPC IPC(8): C07J17/00
CPCC07J17/005
Inventor 俞飚党永军裴成锋王瑞娜张夏衡蒋维马君君李增霞陈小平刘超马玉勇徐鹏
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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