Method for preparing tyrosol glucoside in quantities

A tyrosol glycoside and a large number of technologies are applied in the field of mass preparation of tyrosol glycoside, can solve the problems of increased synthesis cost, complicated synthesis operation, potential safety hazards and the like, and achieve the effects of simple operation, stable process parameters and high yield

Inactive Publication Date: 2010-02-24
FOURTH MILITARY MEDICAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above-mentioned methods are reported in the literature to only obtain gram-level products at one time, and there are certain limitations when expanding the scale of preparation.
In the first method, because the alcoholic hydroxyl group and the phenolic hydroxyl group of tyrosol can all undergo condensation reactions, during large-scale preparation, there are many by-products, and the conditions are difficult to control, resulting in a reduction in yield
In the second method, the active sugar donor tetraacetylglycosyl trichloroacetimide ester needs to be prepared through three-step reactions [Ralph B, Laura M, Robert J, et al. Synthesis and conformational analysis of the T2antigen carbohydrate (β-D- Gal-(1→3)-α-D-GaNAc-OMe). Eur J Org Chem, 2001, 14: 2697-2705.], the synthesis operation is cumbersome and the synthesis cost increases
The third method uses the flammable reducing agent LiAlH 4 , there is a safety hazard in large-scale preparation

Method used

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  • Method for preparing tyrosol glucoside in quantities
  • Method for preparing tyrosol glucoside in quantities
  • Method for preparing tyrosol glucoside in quantities

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Example 1: Mass preparation of tyrosol-β-D-galactoside

[0020] (1) Synthesis of p-Acetoxyphenethyl alcohol

[0021] Dissolve 1.38 kg (10 mol) of tyrosol in 2 L of acetone, add 0.5 L of saturated aqueous sodium hydroxide solution, slowly add 2 L of acetic anhydride, and stir at room temperature for 4 h. The solvent was removed under reduced pressure, the insoluble matter was dissolved with ethyl acetate, washed with distilled water and saturated brine successively until neutral, and concentrated to obtain a colorless oil. Placed in the freezer overnight, white crystals were formed, filtered and washed to obtain 1.53 kg of product, yield 85%, m.p.39-40°C.

[0022] (2) Synthesis of β-D-1-bromo-tetraacetylgalactose

[0023] 20 mL of HClO 4 Slowly added dropwise to 3L of acetic anhydride at 0°C, raised to room temperature, then added 1.08kg (6mol) D-galactose in batches, and reacted at 20°C for 5h. At this temperature, slowly add 0.31kg (10mol) red phosphorus and 580mL ...

Embodiment 2

[0026] Example 2: Mass preparation of tyrosol-β-D-xyloside

[0027] (1) Synthesis of β-D-1-bromo-triacetylxylose

[0028] 20 mL of HClO 4 Slowly added dropwise to 3L of acetic anhydride at 0°C, raised to room temperature, then added 0.675kg (4.5mol) of D-xylose in batches, and reacted at 30°C for 5h. At this temperature, slowly add 0.23kg (7.5mol) red phosphorus and 435mL Br 2 , After reacting for 2h, add 270mL of H 2 O, continue to stir at room temperature for 2h. Add 1.5L CH 2 Cl 2 , filtered to remove insoluble matter, and the filtrate was washed twice with 1.5L ice water, then added to 2.25L cold saturated NaHCO 3 solution, stirred for 20 min, separated, the organic layer was dried with anhydrous magnesium sulfate, filtered, and the solvent was removed to obtain 1.17 kg of light yellow oil with a yield of 68%. The purity can be directly used in the next reaction.

[0029] (2) Synthesis of tyrosol-β-D-xyloside

[0030] The synthetic method of p-acetoxyphenethyl alco...

Embodiment 3

[0032] Embodiment 3: the synthesis of p-Acetoxyphenethyl alcohol (comparative example)

[0033] Dissolve 1.38kg (10mol) of tyrosol in 2L of isopropanol, add 0.5L of saturated aqueous sodium hydroxide solution, and slowly add 2L of acetic anhydride, the reaction system gradually becomes a viscous paste, and the temperature of the reaction system rises significantly, continue to stir 6-8h. The solvent was removed under reduced pressure, the insoluble matter was dissolved with ethyl acetate, washed with distilled water and saturated brine successively until neutral, and concentrated to obtain a colorless oil. 0.58 kg of the product was isolated by column chromatography with a yield of 32%.

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Abstract

The invention discloses a method for preparing tyrosol glucoside in quantities; in the method, tyrosol is taken as raw material, and tyrosol phenolic hydroxyl acetylation protection is carried out selectively to be condensed with acetyl bromide sugar substitute followed by de-protection. The invention features available raw material, less reaction steps, high yield, simple preparation technique, stable technical parameters, capability of preparing kilogram level high purity (more than 98%) tyrosol glucoside once, and application in preparing various tyrosol glucoside.

Description

technical field [0001] The invention relates to a method for preparing tyrosol glycosides in large quantities, and belongs to the technical field of organic synthesis. Background technique [0002] The Tibetan medicine Rhodiola has the reputation of "Plateau Ginseng", and was approved by the Ministry of Health of the former Soviet Union as a "Ginseng-type stimulant". It is an essential health product for astronauts and pilots. Its active ingredient is salidroside. The biological activity of salidroside is significant and diverse. In addition to effectively removing excess free radicals in the body and anti-fatigue effects, it also has anti-radiation, anti-hypoxia, and excitatory central nervous system. And other pharmacological effects, it is regarded as a golden plant. [0003] The inventors used salidroside tyrosol as the lead compound to synthesize a variety of tyrosol glycosides. Preliminary pharmacological tests have proved that tyrosol glycoside has anti-fatigue and ...

Claims

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Application Information

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IPC IPC(8): C07H15/18C07H1/00
Inventor 姜茹孙晓莉石天尧陈惠景临林刘雪英
Owner FOURTH MILITARY MEDICAL UNIVERSITY
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