Method for synthesizing Pro-Xylane through acylation protection and reduction

A Boseine and reducing agent technology, which is applied in the field of Boseine synthesis through acylation protection and reduction, can solve the problems of difficult mass production and difficult removal, and achieve the effect of high selectivity

Active Publication Date: 2021-12-03
SHENZHEN READLINE BIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] However, both of the above two synthetic routes use sodium borohydride as a reducing agent to reduce β-acetone xyloside, which will produce boric acid during the preparation process, and boric acid is very e

Method used

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  • Method for synthesizing Pro-Xylane through acylation protection and reduction
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  • Method for synthesizing Pro-Xylane through acylation protection and reduction

Examples

Experimental program
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Effect test

Embodiment 1

[0053]

[0054] Add 150 ml of methanol, 31.8 g (0.3 mol) of sodium carbonate, 30 g (0.2 mol) of xylose, and 26 g (0.24 mol) of acetylacetone to a 500 ml reaction flask in sequence. After reacting for 12 hours at 80 degrees Celsius, use Adjust the pH to 7 with 4N HCl, spin dry to obtain the crude product of β-acetone xyloside, MS (ESI): m / z: 191.07[M+H] + .

Embodiment 2

[0056]

[0057] All the crude β-acetone xyloside obtained in Example 1 was added into a 500 ml reaction flask, followed by adding 150 ml of pyridine and 24.7 g (0.24 mol) of acetic anhydride, and reacting at 25 degrees Celsius for 24 hours. Add 200 ml of ethyl acetate to dilute, extract with 1 mole per ml of hydrochloric acid solution, use 200 ml each time, extract three times, then extract once with 200 ml of saturated sodium bicarbonate solution, extract once with 100 ml of saturated saline, extract once with 10 g Dry the organic phase with anhydrous sodium sulfate, then add 1.5 g of activated carbon and stir at 50°C for 30 minutes to decolorize, filter with suction, and spin the filtrate to obtain 54.1 g of crude product.

[0058] Use petroleum ether and ethyl acetate in a ratio of 5:2 to prepare 150 ml of a mixed solution, add it to a 500 ml flask containing the crude product, heat and reflux at 60 degrees Celsius and stir, and after it is completely dissolved, slowly co...

Embodiment 3

[0060]

[0061] All the crude β-acetone xyloside obtained in Example 1 was added into a 500 ml reaction flask, 150 ml of pyridine was added, and 33.6 g (0.24 mol) of benzoyl chloride was added dropwise under an ice bath, and the reaction was carried out at 25 degrees Celsius for 24 hours. Add 200 ml of ethyl acetate to dilute, extract with 1 mole per ml of hydrochloric acid solution, use 200 ml each time, extract three times, then extract once with 200 ml of saturated sodium bicarbonate solution, extract once with 100 ml of saturated saline, extract once with 10 g Dry the organic phase with anhydrous sodium sulfate, then add 1.5 g of activated carbon, stir at 50°C for 30 minutes to decolorize, filter with suction, and spin the filtrate to obtain 91.5 g of crude product.

[0062] Use petroleum ether and ethyl acetate in a ratio of 5:2 to prepare 150 ml of a mixed solution, add it to a 500 ml flask containing the crude product, heat and reflux at 60 degrees Celsius and stir, a...

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Abstract

The invention provides a method for synthesizing Pro-Xylane through acylation protection and reduction. The method comprises the following steps: S1) mixing acetylacetone or acetoacetate compounds, xylose and alkaline substances in a solvent, and heating to react to obtain a first intermediate product; s2) carrying out acylation reaction on the first intermediate product and an acylation reagent to obtain a second intermediate product; and s3) carrying out reduction reaction on the second intermediate product and a reducing agent in a solvent to obtain the Pro-Xylane, wherein the reducing agent contains -1-valent hydrogen atoms. Compared with the prior art, the method has the advantages that three hydroxyls in the first intermediate product are acylated through acylation reaction to obtain the intermediate triester, the intermediate triester is easy to purify, and alpha-configuration products can be removed through extraction separation and recrystallization, so that purification in a column chromatography mode is avoided; and the intermediate triester is high in selectivity during reduction, and a strong reducing agent can be used for simultaneously reducing ketone carbonyl and ester groups to directly obtain high-selectivity (S)-Pro-Xylane.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for synthesizing Boseine through acylation protection and reduction. Background technique [0002] Boseine is a xylose derivative with cosmetic and anti-wrinkle effects discovered by L'Oreal for many years. It is converted from xylose and has a wide range of biological activities. Studies have shown that it can rebuild the cell structure by promoting the formation of intercellular mucopolysaccharides, enhance the connection between the dermis and the epidermis, and improve the combination of the dermis and the epidermis, thereby achieving the effect of beauty and anti-wrinkle. [0003] In 2002, L'Oreal's international patent No. WO02 / 051828Al titled Nouveaux dérivés C-glycosides et utilization (new carbon sugar anhydride and its application) was authorized. This patent disclosed the original research and preparation of Boseine for the first time. m...

Claims

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Application Information

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IPC IPC(8): C07D309/10
CPCC07D309/10
Inventor 李振朴廖立新于铁妹潘俊锋刘建
Owner SHENZHEN READLINE BIOTECH CO LTD
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