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Synthetic method of hydroxypropyl tetrahydropyrantriol

A technology of hydroxypropyltetrahydropyrantriol and synthesis method, applied in the field of fine chemicals, can solve problems such as insufficient preparation yield, achieve the effects of high product purity, avoid acid residues, and simple operation

Inactive Publication Date: 2020-08-21
铭颜生物科技(广州)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The above-mentioned prior art requires the use of rare earth metal catalysts, and the preparation yield is also insufficient

Method used

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  • Synthetic method of hydroxypropyl tetrahydropyrantriol
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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030]

[0031] Add 1.5kg of xylose, 1kg of sodium carbonate, 1.4kg of acetylacetone, 15L of water into the reaction bottle, and react at 80-85°C for 20h. After the reaction is completed, return to room temperature, extract with ethyl acetate (3Lx3), and use saturated sodium bisulfate solution Adjust the pH to 4-5, spin the water to obtain a viscous residue, add 10L of ethanol, filter with suction, wash the filter cake with 2L of ethanol, and the obtained mother liquor is directly used for feeding in the next step.

[0032] 1 HNMR (D2O, 400MHz): δ3.79-3.81(m, 1H), 3.62-3.63(m, 1H), 3.43-3.45(m, 1H), 3.31-3.34(m, 1H), 3.19-3.21(m , 1H), 3.11-3.13(t, 1H), 2.92-2.93(m, 1H), 2.58-2.62(m, 1H), 2.25(s, 3H).

[0033]

[0034] Pump the solution obtained in the previous step into the reaction bottle, add 430g of sodium borohydride in batches at 0-5°C, control the reaction temperature not to exceed 40°C during the addition, after the addition is complete, keep the reaction at roo...

Embodiment 2

[0037] Add 1.5kg of xylose, 0.8kg of sodium bicarbonate, 1.4kg of acetylacetone, 15L of water, and react at 95-100°C for 6h in the reaction flask. After the reaction is complete, return to room temperature, extract with ethyl acetate (3L×3), and The sodium bisulfate solution was adjusted to pH=4-5, and the water was spin-dried to obtain a viscous residue. Add 10 L of ethanol, filter with suction, wash the filter cake with 2 L of ethanol, and the obtained mother liquor was directly used for feeding in the next step.

[0038] Pump the solution obtained in the previous step into the reaction bottle, add 350 g of sodium cyanoborohydride in batches at 10-15 ° C, control the reaction temperature during the addition process to not exceed 40 ° C, after the addition is complete, keep the reaction at room temperature for 3 hours, add saturated Sodium bisulfate solution adjusted the pH to 5-6, a large amount of solids precipitated, suction filtered, the solids were washed with 5 L of abso...

Embodiment 3

[0040] Add 1.5kg of xylose, 1kg of sodium carbonate, 1.4kg of acetylacetone, 15L of water, and react at 90-95°C for 10h in the reaction flask. After the reaction is completed, return to room temperature, extract with ethyl acetate (3L×3), and use The sodium solution was adjusted to pH = 4-5, and the water was spin-dried to obtain a viscous residue. Add 10 L of ethanol, filter with suction, wash the filter cake with 2 L of ethanol, and the obtained mother liquor was directly used for feeding in the next step.

[0041] Pump the solution obtained in the previous step into the reaction bottle, add 350 g of sodium triacetylborohydride in batches at 30-40 ° C, control the reaction temperature during the addition process to not exceed 40 ° C, after the addition is completed, keep the reaction at room temperature for 3 hours, add saturated The sodium bisulfate solution was used to adjust the pH to 5-6, a large amount of solids were precipitated, filtered by suction, the solids were was...

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Abstract

The invention discloses a synthetic method of hydroxypropyl tetrahydropyrantriol, belonging to the technical field of fine chemicals. Xylose is used as a raw material and is subjected to a two-step reaction to prepare hydroxypropyl tetrahydropyrantriol. The synthetic method is simple in preparation process, preparation yield is high, reagents are cheap and easy to obtain, and good industrial prospects are obtained.

Description

technical field [0001] The invention relates to the technical field of fine chemicals, in particular to a method for synthesizing hydroxypropyltetrahydropyrantriol. Background technique [0002] Hydroxypropyltetrahydropyranotriol, also known as Bosein, is a xylose derivative with anti-aging active substances, which can promote the synthesis of collagen, make the skin stronger and more elastic, and improve fine lines on the neck , Prevent aging. Bosein can induce the biosynthesis of GAGs mucopolysaccharides and PG proteoglycans in the superficial skin layer, and the absence of GAGs and PGs will lead to a decrease in skin moisture content and reduced defense capabilities; it can effectively promote the tight junction between the epidermis and the dermis, and better fix the dermis , the skin is stronger and more elastic; long-term use can effectively improve wrinkles and fine lines on the face and neck, and promote the regeneration of damaged tissues. It is widely used in cos...

Claims

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Application Information

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IPC IPC(8): C07D309/10
CPCC07D309/10
Inventor 胡柏林
Owner 铭颜生物科技(广州)有限公司
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