A kind of preparation method of 6,6'-bis(2,3-dimethoxybenzoyl)-α,α-d-trehalose and its intermediate

A technology of dimethoxybenzoyl and dimethoxybenzoic acid, which is applied in the field of preparation of 6,6'-bis-α,α-D-trehalose and its intermediates, can solve the problem that is not suitable for large-scale Production, difficult to remove triphenoxyphos, difficult to completely remove and other problems, to achieve the effect of increased yield, easy removal, and high yield

Active Publication Date: 2017-03-01
济南美高生物医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in this synthetic method, since the benzyl protecting group needs to be catalyzed by hydrogenation, and it is difficult to completely remove it, it needs to be separated and prepared by column chromatography, which is not suitable for large-scale production; in addition, diisopropyl azodicarboxylate is used in this patent method Ester and triphenylphosphine are condensation reagents (Mitsunobu reaction), because the triphenoxyphosphine generated is difficult to remove, and column chromatography is required for separation and preparation, which is also not suitable for large-scale production

Method used

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  • A kind of preparation method of 6,6'-bis(2,3-dimethoxybenzoyl)-α,α-d-trehalose and its intermediate
  • A kind of preparation method of 6,6'-bis(2,3-dimethoxybenzoyl)-α,α-d-trehalose and its intermediate
  • A kind of preparation method of 6,6'-bis(2,3-dimethoxybenzoyl)-α,α-d-trehalose and its intermediate

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Embodiment 1

[0032] Example 1: Preparation of 6,6'-bis(2,3-dimethoxybenzoyl)-α,α-D-trehalose intermediate

[0033] Dissolve 5.46 g of 2,3-dimethoxybenzoic acid in 60 mL of anhydrous tetrahydrofuran, add 4.86 g of N,N'-carbonyldiimidazole, and stir at room temperature for 30 minutes. Add 7.75 g of the compound shown in II and 0.16 g of N-bromosuccinimide in a catalytic amount, and stir for 8 hours to react. Thin layer chromatography showed the reaction was complete. 60 mL of water was added to the reaction solution, stirred for 10 minutes, and extracted three times with 50 mL of dichloromethane. The organic layers were combined, washed three times with saturated potassium carbonate aqueous solution, then with saturated brine, and dried over anhydrous sodium sulfate. Filter and concentrate. Recrystallize the residue with 50 mL of ethanol / water (2 / 1) to obtain 10.3 g of the compound represented by formula III, which is 6,6'-bis(2,3-dimethoxybenzoyl)-α,α -D-trehalose intermediate, yield 93...

Embodiment 2

[0037] Example 2: Preparation of 6,6'-bis(2,3-dimethoxybenzoyl)-α,α-D-trehalose (scale-up test)

[0038] Dissolve 273 grams of 2,3-dimethoxybenzoic acid in 2.5 L of anhydrous tetrahydrofuran, add 243 grams of N,N'-carbonyldiimidazole, and stir at room temperature for 30 minutes. Add 388 grams of the compound shown in II and 8 grams of N-bromosuccinimide in a catalytic amount, and stir for 12 hours to react. Thin layer chromatography showed the reaction was complete. 2.5 L of water was added to the reaction solution, stirred for 10 minutes, and extracted three times with 1.25 L of dichloromethane. The organic layers were combined, washed three times with saturated potassium carbonate aqueous solution, then with saturated brine, and dried over anhydrous sodium sulfate. Filter and concentrate. The residue was recrystallized with 1.5 L of ethanol / water (2 / 1, volume ratio) to obtain 498 g of the compound represented by formula III, with a yield of 90%.

[0039] Dissolve 504 g o...

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Abstract

The invention discloses a method for preparing a 6,6'-bi(2,3-dimethoxyphenyl)-alpha,alpha-D-trehalose intermediate. The method comprises the following steps: (1) dissolving 2,3-dimethoxybenzoic acid in anhydrous tetrahydrofuran, adding N,N'-carbonyl diimidazole, stirring at room temperature, and performing carboxyl activation; (2) adding a compound shown as a formula II and N-bromo-succinimide in a catalytic amount into the reaction solution subjected to carboxyl activation in the step (1), stirring and reacting; and (3) adding water into the solution reacted in the step (2), stirring for 10-15 minutes, extracting for three times by using dichloromethane, mixing the organic layers, washing for three times by using a saturated potassium carbonate aqueous solution, washing by using saturated salt, drying by using anhydrous sodium sulfate, filtering, concentrating, recrystallizing the residues by using ethanol / water, thereby obtaining the 6,6'-bi(2,3-dimethoxyphenyl)-alpha,alpha-D-trehalose intermediate, removing the trimethylsilyl of the intermediate under weakly acidic conditions, thereby obtaining 6,6'-bi(2,3-dimethoxyphenyl)-alpha,alpha-D-trehalose. The method disclosed by the invention is mild in reaction conditions, low in cost and suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of 6,6'-bis(2,3-dimethoxybenzoyl)-α,α-D-trehalose and its intermediate, belonging to the technical field of organic synthesis. Background technique [0002] Tumor invasion refers to the malignant tumor cells leaving the primary tumor to attack the surrounding tissue, which is marked by tumor cells breaking through the basement membrane. Tumor metastasis refers to the process in which malignant tumor cells separate from the primary tumor, transfer to other tissues or organs to continue to grow, and form secondary tumors with the same properties as the primary tumor. Tumor invasion is the prelude to tumor metastasis, and tumor metastasis is the continuation and result of invasion, and the two are closely related. Tumor invasion and metastasis are the basic characteristics of malignant tumors and the main cause of death of clinical tumor patients (more than 90%). How to prevent and treat tumor metastasis has...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H23/00C07H1/00C07H13/08
Inventor 刘兆鹏刘郁婧
Owner 济南美高生物医药科技有限公司
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