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Preparation method of 1,6,7-trihydroxy-3-methoxybifeniprone-2-c-β-d-glucopyranoside

A methylation and compound technology, applied in the field of chemical synthesis, can solve the problems of methylation reagents such as high toxicity, low yield, and poor selectivity, and achieve significant application value and economic benefits, high product yield, and low cost Effect

Active Publication Date: 2016-03-02
KPC PHARM INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The advantage of this method is that the raw materials are easy to obtain and the reaction steps are short; but this method also has significant disadvantages, namely, the methylation reagent is highly toxic, dangerous, and the selectivity of the reaction is poor, and it is necessary to separate the product by column chromatography. The rate is not high, only 20% to 30%

Method used

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  • Preparation method of 1,6,7-trihydroxy-3-methoxybifeniprone-2-c-β-d-glucopyranoside

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Experimental program
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Effect test

Embodiment 1

[0034] The preparation of compound shown in embodiment 1 formula IV

[0035] Weigh 4.22g (0.01mol) of compound of formula II and 1.24g (0.02mol) of boric acid and dissolve in 200ml of N,N-dimethylformamide, and stir at room temperature for 1 hour. Add 1.76g (0.02mol) potassium carbonate, 3.60g (0.04mol) dimethyl carbonate to the reaction solution, heat the mixture, reflux and stir for 10 hours and let it cool, the concentrated reaction solution has a yellow solid precipitated, filtered, removed After washing with ion water and drying, 3.81 g of yellow powdery solid was obtained, which was the compound shown in formula IV, and the product yield was 85.6%. 1 HNMR (DMSO): δ13.68(s, 2H), δ7.08(s, 2H), δ6.62(s, 2H), δ6.32(s, 2H), δ5.35(s, 2H), δ4.96 (d, 2H), δ3.85 (s, 6H), δ3.79~3.40 (m, 18H).

Embodiment 2

[0036] Preparation of compound shown in embodiment 2 formula IV

[0037] Weigh 4.22g (0.01mol) of the compound of formula II and 1.24g (0.02mol) of boric acid and dissolve in 200ml of dimethyl sulfoxide, and stir at room temperature for 1 hour. Add 1.76g (0.02mol) of potassium carbonate and 3.60g (0.04mol) of dimethyl carbonate to the reaction solution, heat the mixture, reflux for 10 hours and allow it to cool, the concentrated reaction solution has a yellow solid precipitated, filtered, deionized After washing with water and drying, 3.74 g of a yellow powdery solid was obtained, which was the compound represented by formula IV, and the product yield was 84.0%. 1 HNMR (DMSO): δ13.68(s, 2H), δ7.08(s, 2H), δ6.62(s, 2H), δ6.32(s, 2H), δ5.35(s, 2H), δ4.96 (d, 2H), δ3.85 (s, 6H), δ3.79~3.40 (m, 18H).

Embodiment 3

[0038] Preparation of compound shown in embodiment 3 formula IV

[0039] Weigh 4.22g (0.01mol) of compound of formula II and 1.24g (0.02mol) of boric acid and dissolve in 200ml of 1,4-dioxane, and stir at room temperature for 1 hour. Add 1.76g (0.02mol) of potassium carbonate and 3.60g (0.04mol) of dimethyl carbonate to the reaction solution, heat the mixture, stir and react under slight reflux for 10 hours, then let it cool, and the concentrated reaction solution has a yellow solid precipitated, filtered, After washing with deionized water and drying, 3.93 g of a yellow powdery solid was obtained, which was the compound shown in formula IV, and the product yield was 88.3%. 1 HNMR (DMSO): δ13.68(s, 2H), δ7.08(s, 2H), δ6.62(s, 2H), δ6.32(s, 2H), δ5.35(s, 2H), δ4.96 (d, 2H), δ3.85 (s, 6H), δ3.79~3.40 (m, 18H).

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Abstract

The invention relates to the field of chemical synthesis, and specifically disclose a preparation method of 1,6,7-trihydroxy-3-methoxyl xanthone-2-C-beta-D-glucopyranoside. According to the method, mangiferin is adopted as a raw material, and 3-methoxyl mangiferin is prepared through boric acid esterification, selective methylation, and hydrolysis reactions. The method provided by the invention has the advantages of short synthesis route, high product yield, low-toxic safe reagent, low production cost, and suitability for large-scale industrial productions.

Description

technical field [0001] The invention relates to the field of chemical synthesis, and specifically discloses a method for preparing 1,6,7-trihydroxy-3-methoxybifenapyrone-2-C-β-D-glucopyranoside. Background technique [0002] 3-Methoxymangiferin, the full name is 1,6,7-trihydroxy-3-methoxybisfeniprone-2-C-β-D-glucopyranoside, also known as homomangiferin, which is C- Glycoside xanthone compounds are present in plants such as Anacardaceae plants Mango (Mangifera indica L.), almond (Mangifera persiciformis C.), and its structural formula is as shown in formula I: [0003] [0004] Currently, there are three main ways to obtain 3-methoxymangiferin: [0005] (1) Plant extraction method. First extract the crude mangiferin from mango, almond and other plants, and then further separate the crude mangiferin to obtain 3-methoxymangiferin. For example, Masakazu Aritomi et al. used column chromatography to separate high mangiferin from crude mangiferin (MasakazuAritomiandToshiokaw...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D407/04
Inventor 宋立明张伟高小惠杨旭娟
Owner KPC PHARM INC