Synthesizing method of piceatannol 3'-O-belta-D-glucopyranoside

A synthesis method and a technique for tristilbene glycosides are applied in the field of compound synthesis and can solve problems such as chemical synthesis of tristilbene glycosides that have not yet been seen

Active Publication Date: 2017-09-26
KPC PHARM INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

So far, this compound has only been isolated from Tibet rhubarb and Lhasa rhubarb, and there is no report on the chemical synthesis of trizaperone

Method used

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  • Synthesizing method of piceatannol 3'-O-belta-D-glucopyranoside
  • Synthesizing method of piceatannol 3'-O-belta-D-glucopyranoside
  • Synthesizing method of piceatannol 3'-O-belta-D-glucopyranoside

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0104] Embodiment 1, preparation formula S1 compound

[0105]

[0106] 3,4-Dihydroxybenzaldehyde (5.0 g, 36.2 mmol) was dissolved in N,N-dimethylformamide (100 ml), and sodium carbonate (9.59 g, 90.6 mmol) was added thereto. After stirring at room temperature for 5 minutes, allyl bromide (3.13ml, 36.2mmol) was slowly added dropwise thereto. Continue to stir and react at room temperature for 12 hours. After the reaction is completed, use diatomaceous earth to filter and collect the filtrate. The oil obtained after the filtrate was concentrated under reduced pressure was subjected to silica gel column chromatography (petroleum ether: ethyl acetate = 9:1) to obtain the compound of formula S1 (4.4 g, yield 68%) as a white solid.

[0107] The structural identification of the compound of formula S1 is as follows:

[0108] 1 H NMR (500MHz, CDCl 3 )δ9.82(s,1H),7.44(d,J=2.0Hz,1H),7.39(dd,J=8.3,2.0Hz,1H),6.95(d,J=8.3Hz,1H),6.09- 6.01(m,1H),5.97(br.s,1H),5.42(ddd,J=17.3,2.8,1.6Hz...

Embodiment 2

[0109] Embodiment 2, preparation formula II compound

[0110]

[0111]The compound of formula S1 (534 mg, 3.0 mmol) was dissolved in dichloromethane (15 mL), and imidazole (347 mg, 5.1 mmol) and tert-butyldimethylsilyl chloride (634 mg, 4.2 mmol) were added sequentially at room temperature, and reaction 5 Hours later, add saturated sodium bicarbonate solution to the reaction system, dichloromethane extraction three times, 30 mL each time, combine the organic phases and wash with saturated brine, dry with anhydrous sodium sulfate, filter, and concentrate the filtrate under reduced pressure to obtain The oil was subjected to flash silica gel column chromatography (petroleum ether: ethyl acetate = 40:1) to obtain the compound of formula II (867 mg, yield 99%).

[0112] Formula II compound is carried out structural identification as follows:

[0113] 1 H NMR (500MHz, CDCl 3 )δ9.81(s,1H),7.44(dd,J=8.3,2.0Hz,1H),7.37(d,J=2.0Hz,1H),6.95(d,J=8.3Hz,1H),6.11– 6.03(m,1H),5.43(dq,J...

Embodiment 3

[0114] Embodiment 3, preparation formula S2 compound

[0115]

[0116] 3,5-Dihydroxybenzoic acid (5.0 g, 32.4 mmol) was dissolved in N,N-dimethylformamide (100 ml). Cesium carbonate (53.0 g, 162 mmol) was added thereto, and after stirring at room temperature for 5 minutes, allyl bromide (11.2 ml, 129.6 mmol) was slowly added dropwise to the reaction system. Under the protection of nitrogen, the reaction was carried out at room temperature for 12 hours. After the reaction, filter through celite and collect the filtrate. Concentrate under reduced pressure to remove most of N,N-dimethylformamide, dissolve the remaining sample in ethyl acetate (50ml), and wash with water three times, 50mL each time. The organic phase was washed once with saturated brine (50ml). The organic phase was collected and concentrated under reduced pressure to obtain the compound of formula S2 (8.28 g, yield 93%) as light yellow oil.

[0117] The structural identification of the compound of formula ...

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Abstract

The invention belongs to the field of synthesizing of compounds, and particularly relates to a synthesizing method of piceatannol 3'-O-belta-D-glucopyranoside. The synthesizing method is characterized in that a compound in a formula VIII is reacted, so as to obtain the piceatannol 3'-O-belta-D-glucopyranoside shown in a formula I, wherein in the formula VIII, R<4> is acetyl, benzyl, allyl or alloc. The synthesizing method has the advantages that the compound of piceatannol 3'-O-belta-D-glucopyranoside is synthesized; the cost of the used reagent is low, and the obtaining is easy; the operation is simple, and the total yield rate is 26%; a simple, efficient and environment-friendly piceatannol 3'-O-belta-D-glucopyranoside synthesizing route is provided, a first path is opened for the chemical synthesizing of the piceatannol 3'-O-belta-D-glucopyranoside, and the important meaning is realized in the field of medicines. The formula I and the formula VIII are shown in the description.

Description

technical field [0001] The invention belongs to the field of compound synthesis, and in particular relates to a synthesis method of tristilbene. Background technique [0002] Stilbene is a chemical component extracted and isolated from the roots or rhizomes of Rheum lhasaense A.J.Li et P.K.Hsiao and Rheum tibeticum Maxim.ex Hook.f. Styrene glycosides. The chemical name of tristilbene glycoside is Piceatannol 3′-O-β-D-glucopyranoside, the English name is Piceatannol 3′-O-β-D-glucopyranoside, and the molecular formula is C 20 h 22 o 9 , the structural formula is as follows: [0003] [0004] Existing studies have shown that stilbeneside has a variety of pharmacological activities, such as improving microcirculatory disturbance, neuroprotection, anti-oxidation, and scavenging free radicals, making it have potential clinical application value in the prevention and treatment of cardio-cerebral ischemia. [0005] CN102659861A discloses a method for purifying tristilbeside....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/203C07H1/00
CPCC07H1/00C07H15/203
Inventor 李大山李瑞熙李剑峰杨兆祥
Owner KPC PHARM INC
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