A method for synthesizing tenuifoliside B

A technology of acetoxyl and sucrose, applied in the field of chemical synthesis of natural product TenuifolisideB, can solve the problem of no TenuifolidiseB chemistry, etc., and achieve the effects of cheap and controllable cost, few by-products, and high conversion rate

Active Publication Date: 2015-12-09
ZHEJIANG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Currently, there is no report on the chemical synthesis of TenuifoliadiseB

Method used

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  • A method for synthesizing tenuifoliside B
  • A method for synthesizing tenuifoliside B
  • A method for synthesizing tenuifoliside B

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] 4-Acetoxy-3,5-dimethoxycinnamic acid ( 7 ) preparation:

[0025] Syringaldehyde ( 2 ) 60.06g (330mmol) was dissolved in 360mL pyridine, 36.72g (360mmol) of acetic anhydride was added, refluxed for 2 hours, cooled to room temperature, and directly put into the next reaction, adding 500mL of benzene, 52.00g (500mmol) of malonic acid, piperidine 5mL, install a reflux device with a water separator, oil bath, stir to dissolve, and reflux for 3 hours. After completion of the reaction, cool to room temperature, add 1000mL saturated sodium bicarbonate solution, stir, separate the water layer, acidify with 6mol / L hydrochloric acid to a pH value of about 5, filter, rinse the filter cake with 500ml water, and dry to obtain a white solid 4 -Acetoxy-3,5-dimethoxycinnamic acid ( 7 ) 56.18g, yield 64%. Melting point, spectral data, and high-resolution mass spectrometric data of 4-acetoxy-3,5-dimethoxycinnamic acid: melting point 202-204°C; =+0.2 (c=1.01, MeOH); 1 HNMR (500MHz, ...

Embodiment 2

[0027] 4-acetoxybenzoic acid ( 6 ) preparation:

[0028] p-Hydroxybenzoic acid ( 3 ) 4.55g (33mmol) was dissolved in 30mL pyridine, 3.67g (36mmol) of acetic anhydride was added, and refluxed for 2 hours. After completion of the reaction, cool to room temperature, add 100mL saturated sodium bicarbonate solution, stir, separate the water layer, acidify with 6mol / L hydrochloric acid to a pH value of about 2, filter, rinse the filter cake with 50ml water, and dry to obtain a white solid 4 -Acetoxybenzoic acid ( 6 ) 5.50g, the yield is 93%. Melting point, spectral data, and high-resolution mass spectrometry data of 4-acetoxybenzoic acid: melting point 191-193°C; 1 HNMR (500MHz, CD 3 OD): δ=8.06 (m, J =8.5, 2.5Hz, 2H), 7.21 (m, J =8.5, 2.5Hz, 2H), 2.29 (s, 3H) ppm; 13 CNMR (125MHz, CD 3 OD): δ=170.7, 169.1, 156.1, 132.4 (2C), 129.6, 123.0 (2C), 21.0ppm; HRMS (ESI): 181.0498 (calcd.forC 9 h 9 o 4 [M+H] + 181.0501).

Embodiment 3

[0030] 4-Acetoxy-3,5-dimethoxycinnamic anhydride ( 8 ):

[0031] 4-Acetoxy-3,5-dimethoxycinnamic acid ( 7 ) 31.92g (120mmol) was dissolved in 4000mL anhydrous ethyl acetate, 16.5mL (120mmol) of anhydrous triethylamine was added, cooled in an ice bath, 5.94g (20mmol) of triphosgene was added at 0°C under stirring, and the reaction was 10 minutes; react at room temperature for 20 minutes. Filter, wash the filter cake with anhydrous ethyl acetate (1000mL), combine the filtrate and washings, evaporate the solvent, and dry to obtain a white solid 4-acetoxy-3,5-dimethoxycinnamic anhydride ( 8 ), directly into the next reaction without purification, the yield is about 82%.

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Abstract

The invention provides a synthetic method of Tenuifoliside B. Sucrose, syringaldehyde and p-hydroxybenzoic acid are used as the starting materials, and subjected to 6 steps of chemical conversion reactions to realize total synthesis of Tenuifoliside B for the first time. The raw materials of sucrose, syringaldehyde and p-hydroxybenzoic acid employed by the invention are convenient, easily available and at controllable low cost; each step of chemical reaction has mild reaction conditions and is easy to implement and operate in the practical application; each step of chemical reaction has high reaction conversion rate, especially the first three reaction steps have mild reaction conditions, simple operations, high yield, small amount of by-products and total yield at about 22.3%; and the Tenuifoliside B can be directly used for subsequent steps of the synthesis reaction without fine column chromatography purification.

Description

technical field [0001] The invention belongs to the field of chemical synthesis and relates to a chemical synthesis method of natural product Tenuifoliside B with brain protection effect. Background technique [0002] TenuifolisideB (compound 1) is obtained from the traditional Chinese medicine polygala ( Polygalate nuifolia Willd.) isolated sugar esters (YukinobuIkeya, KoSugama, MinoruOkada, HiroshiMitsuhashi. Chem. PharmBull. ,1991,39(10),2600-2605.), is a natural product. The chemical structural formula of the natural product (TenuifolisideB) is as follows: [0003] [0004] The results of pharmacological experiments show that Tenuifoliside B (3-10mg / kg, p.o. ) has a significant improvement effect on the memory deficits induced by scopolamine and sodium cyanide in rats, which is similar to the activity of the positive drug tacrine (YukinobuI, ShigefumiT, MitsuoT, HumitoK, KouinT, TakujiYandMasakiA. Biol. and Pharm. Bulletin. ,2004,27,1081-1085.), can be used to ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H13/08C07H1/00
Inventor 栾连军施琦渊吴永江
Owner ZHEJIANG UNIV
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