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Method for synthesizing glassine

A technology of Boseine and ice-water mixture, which is applied in the field of Boseine synthesis by tandem reaction, which can solve the problems of short synthesis route, increased metal residues in products, and difficulties in product separation and purification.

Active Publication Date: 2021-05-18
HEBEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Patent document CN 202010643748.9 discloses a method for preparing Boseine by Knoevenagel condensation of xylose and acetylacetone in alkaline solution, followed by reduction with sodium borohydride. This method has been reported in the literature ((a) A .Cavezza et al.Bioorg.Med.Chem.Lett.2009,19,845; (b) Huang Dongting et al. Guangdong Chemical Industry, 2018,10,73.), although this method has a short synthetic route and only two chemical reactions, but , using water as the reaction solvent, resulting in difficulty in product separation and purification; patent document CN 201910785216.6 discloses a one-pot method for synthesizing Bose using rare earth metal complexes to catalyze the Knoevenagel condensation of xylose and ethyl acetoacetate, and then reducing it with isopropanol Because of the method, the yield is up to 80%. Although this method has improved the method in the journal literature, due to the use of a homogeneous metal catalyst, the metal residue in the product will inevitably increase; the patent document CN 2020010629023.4 discloses a A one-pot method for preparing Boseine by using isopropanol dehydrogenase and Boseine synthetase, the yield can reach 89.5%
This method is greener than chemical methods, but product purification is difficult

Method used

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  • Method for synthesizing glassine

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Experimental program
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Effect test

Embodiment 1

[0034] Step a, the synthesis of compound (E)-(2R,3S,4S)-2,3,4-tribenzyloxypent-6-acetylhex-5-enal:

[0035] Dissolve (2R,3S,4S)-2,3,4-tribenzyloxyglutaraldehyde (4.18g, 10mmol) and acetone (0.58g, 11mmol) in ethanol (15mL), and add dropwise to a mass concentration of 50% Sodium hydroxide solution (0.4mL), 27 ℃ insulation reaction for 14 hours, there is precipitate generation, and reaction solution is poured into ice water (100mL), drips glacial acetic acid (1mL) (neutralizes the pH value of solution to 7- 8), extracted with ethyl acetate (15mL×3), the organic phase was washed successively with water (10mL×3), saturated brine (10mL×1), dried over anhydrous sodium sulfate, concentrated and crystallized, filtered to obtain (E) -(2R,3S,4S)-2,3,4-tribenzyloxypent-6-acetylhex-5-enal (4.2 g, yield 91%). 1 H NMR (CDCl 3 400MHz): δ2.09(s,3H,COCH 3 ),3.91(d,1H,H-2,J=5.2Hz),4.07(d,1H,H-4,J=3.2Hz),4.09-4.12(m,1H,H-3),4.48-4.76 (m,6H,3×CH 2 Ph), 6.26(dd, 1H, CH=CHCO, J=12.8, 6.0Hz), ...

Embodiment 2

[0041] Other steps are the same as in Example 1, except that sodium hydroxide in step a is replaced by potassium carbonate; acetic acid is replaced by hydrochloric acid (1 mol / liter).

Embodiment 3

[0043] Other steps are the same as in Example 1, except that the sodium hydroxide in step a is replaced by N,N-dimethylethane-1,2-diamine and 2,2-dimethyl-1,3-diamine Two substances of oxane-4,6-dione, wherein the molar weight of N,N-dimethylethane-1,2-diamine is (2R,3S,4S)-2,3,4-tri 10% of benzyloxyglutaraldehyde, the molar mass of 2,2-dimethyl-1,3-dioxane-4,6-dione is (2R,3S,4S)-2,3,4- 30% of Tribenzyloxyglutaraldehyde.

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Abstract

The invention relates to a method for synthesizing a glassine. The method comprises the following steps: reacting (2R, 3S, 4S)-2, 3, 4-tribenzyloxy glutaraldehyde with acetone to synthesize a key intermediate (E)-(2R, 3S, 4S)-2, 3, 4-tribenzyloxy pentyl-6-acetyl hexane-5-olefine aldehyde, then catalyzing (E)-(2R, 3S, 4S)-2, 3, 4-tribenzyloxy pentyl-6-acetyl hexane-5-olefine aldehyde with Lewis acid to sequentially carry out a nucleophilic addition and a 1, 4-Michael addition reactions, obtaining benzyl-protected Pro-Xylane<TM> 1-((2S, 3S, 4S, 5R)-3, 4, 5-tri(benzyloxy) tetrahydro-2H-pyran-2-yl)propan-2-ol, and finally, carrying out catalytic hydrogenation by using palladium carbon to remove benzyl, so as to obtain Pro-XylaneTM (2S, 3R, 4S, 5R)-2-(2-hydroxypropyl) tetrahydro-2H-pyran-3, 4, 5-triol. The method is high in reaction yield, the obtained product is high in purity, and the method has huge application value.

Description

technical field [0001] The invention belongs to the fields of organic synthesis, fine chemicals and daily chemicals, and in particular relates to a method for synthesizing Boseine by means of series reactions. Background technique [0002] Bosein (Pro-Xylane TM ), full name (2S,3R,4S,5R)-2-(2-hydroxypropyl)tetrahydro-2H-pyran-3,4,5-triol, referred to as hydroxypropyl tetrahydropyrantriol (CAS: 439685-79-7). Boseine is a bioactive substance derived from natural xylose, which can activate the synthesis of mucopolysaccharides (GAGs), promote the production of hyaluronic acid and collagen; Boseine can also improve the adhesion between the dermis and epidermis It promotes the synthesis of collagen VII and collagen IV, regenerates damaged tissues, maintains the elasticity of the dermis, and prevents skin aging (Guo Li. Chinese Cosmetics, 2020,10,80.). [0003] Patent document CN 202010643748.9 discloses a method for preparing Boseine by Knoevenagel condensation of xylose and ac...

Claims

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Application Information

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IPC IPC(8): C07D309/10
CPCC07D309/10Y02P20/55
Inventor 古国贤王英明李明凯孙树政杨延琴张自生郭宏飞
Owner HEBEI UNIV OF TECH
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