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Method for synthesizing cosmetic active material hydroxypropyl tetrahydropyrantriol through one-pot method under promoting of rare earth metal coordination compound

A rare earth metal, Boseine technology, applied in organic compound/hydride/coordination complex catalysts, physical/chemical process catalysts, organic chemistry, etc. The effect of cheap and readily available reagents

Inactive Publication Date: 2019-11-19
SHANGHAI COACHCHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For the synthesis method of Bosein, although there are some reports in the literature, it often requires several steps of reaction, the process is complicated, and the cost is high.

Method used

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  • Method for synthesizing cosmetic active material hydroxypropyl tetrahydropyrantriol through one-pot method under promoting of rare earth metal coordination compound
  • Method for synthesizing cosmetic active material hydroxypropyl tetrahydropyrantriol through one-pot method under promoting of rare earth metal coordination compound
  • Method for synthesizing cosmetic active material hydroxypropyl tetrahydropyrantriol through one-pot method under promoting of rare earth metal coordination compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014]

[0015] Add 150 grams of isopropanol, 30 grams (0.2mol) of xylose, 1.2 grams (0.002 mol) of catalyst, and 26 grams (0.2mol) of ethyl acetoacetate successively in the reaction flask of 500ml, after reacting for 36 hours at 80 degrees centigrade, Extracted three times with water and ethyl acetate. The aqueous layer was removed, and the organic layer was dried over anhydrous sodium sulfate. The solvent was removed by a rotary evaporator to obtain 32.5 g of Bosene with a yield of 85%.

Embodiment 2

[0017]

[0018] Add 150 grams of isopropanol, 30 grams (0.2mol) of xylose, 1.3 grams (0.002 mol) of catalyst, and 26 grams (0.2mol) of ethyl acetoacetate successively in the reaction flask of 500ml, after reacting for 36 hours at 80 degrees Celsius, Extracted three times with water and ethyl acetate. The aqueous layer was removed, and the organic layer was dried over anhydrous sodium sulfate. The solvent was removed by a rotary evaporator to obtain 31.2 g of Bosene with a yield of 81%.

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Abstract

The invention belongs to the fields of organic synthesis, fine chemicals and daily chemicals, and particularly relates to a method for synthesizing hydroxypropyl tetrahydropyrantriol from xylose and ethyl acetoacetate through a one-pot method under the promoting of a rare earth metal coordination compound. According to the present invention, the method has characteristics of easy operation, inexpensive and easily available reagents and good industrial application prospects.

Description

technical field [0001] The invention belongs to the fields of organic synthesis, fine chemicals and daily chemicals, and specifically relates to a one-pot method for synthesizing Boseine from xylose and ethyl acetoacetate promoted by rare earth metal complexes. Background technique [0002] Boseine, also known as hydroxypropyltetrahydropyranotriol (CAS No. 439685-79-7), is a biologically active substance that can fight against skin aging, dehydration and other symptoms, and is widely used in food, biology, medicine, Cosmetics and many other fields. For the synthesis method of Bosene, although there are some literature reports at present, it often requires several steps of reaction, the process is complicated, and the cost is high. The invention provides a method for synthesizing Boseine by utilizing xylose and ethyl acetoacetate in one pot. The method is characterized by using a rare earth metal complex as a catalyst, which can not only promote the glycosylation reaction o...

Claims

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Application Information

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IPC IPC(8): C07D309/10B01J31/22
CPCB01J31/184B01J2531/35C07D309/10
Inventor 吴江张伟朱纯银
Owner SHANGHAI COACHCHEM TECH
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