Method for synthesizing panaxytriol

A technology of panaxatriol and diol, which is applied in chemical instruments and methods, preparation of oxygen-containing compounds, preparation of hydroxyl compounds, etc., and can solve the problems of long synthesis route and low synthesis yield of panaxatriol

Active Publication Date: 2012-03-28
PAPANNA BEIJING TECH
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  • Abstract
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  • Claims
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Problems solved by technology

[0005] Based on the above reasons, through long-term research, in order to solve the problems of long synthetic routes and low synthetic yields of panaxatriol, the purpose of the present invention is to provide a method with few reaction steps, mild reaction conditions and high yield. Method for preparing panaxatriol with high efficiency and good stereoselectivity

Method used

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  • Method for synthesizing panaxytriol
  • Method for synthesizing panaxytriol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] preparation Panaxytriol (I)

[0055] 0.0118g (0.12 mmol) cuprous chloride, 0.16mL n-butylamine, 0.37mL water, 0.118 g (0.6mmol) (4 R ,5 R )-dodecane-1-yne-4,5-diol in dichloromethane (9mL) solution was slowly added 0.144g (0.9mmol) ( R )-5-bromo-1-penten-4-yn-3-ol, 0.2081g (3mmol) hydroxylamine hydrochloride aqueous solution 2mL, keep the system light yellow, after the dropwise addition, continue to react for 1h. After the reaction, extract with dichloromethane, combine the organic phases, dry over anhydrous sodium sulfate, filter, concentrate, and perform silica gel column chromatography (petroleum ether: ether, 5:1) to obtain 0.14 g of light yellow oily liquid (yield: 85 %). [α] D 20 = -20.8 (c = 1.1, CHCl 3 ); 1 H NMR (300 MHz, CDCl 3 ): δ 5.95 (ddd, J = 17.04, 10.11, 5.31 Hz 1H), 5.44-5.50 (m, 1H), 5.23-5.27 (m, 1H), 4.90-4.94 (m, 1H), 3.62 (m, 2H ), 2.58 (m, 2H), 2.11 (br 3H), 1.25–1.58 (m, 12H), 0.88 (t, J = 6.87 Hz 3H); 13 C NMR (75 MHz, CDCl 3 ): Δ...

Embodiment 2

[0057] preparation Panaxytriol ( Ⅰ )

[0058] 0.0177g (0.12 mmol) cuprous bromide, 0.16mL ethylamine, 0.37mL water, 0.118g (0.6mmol) (4 R ,5 R )-dodecane-1-yne-4,5-diol in chloroform (9mL) solution was slowly added 0.144g (0.9mmol) ( R )-5-bromo-1-penten-4-yn-3-ol, 0.2081g (3mmol) hydroxylamine hydrochloride aqueous solution 2mL, keep the system light yellow, after the dropwise addition, continue to react for 1h. After the reaction, extract with chloroform, combine the organic phases, dry over anhydrous sodium sulfate, filter, concentrate, and perform silica gel column chromatography (petroleum ether: ether, 5:1) to obtain 0.14 g of light yellow oily liquid (85% yield) . [α] D 20 = -20.8 (c = 1.1, CHCl 3 ); 1 H NMR (300 MHz, CDCl 3): δ 5.95 (ddd, J = 17.04, 10.11, 5.31 Hz 1H), 5.44-5.50 (m, 1H), 5.23-5.27 (m, 1H), 4.90-4.94 (m, 1H), 3.62 (m, 2H ), 2.58 (m, 2H), 2.11 (br 3H), 1.25–1.58 (m, 12H), 0.88 (t, J = 6.87 Hz 3H); 13 C NMR (75 MHz, CDCl 3 ): Δ136.41, 117.6...

Embodiment 3

[0073] (4 R ,5 R )-dodecane-1-yne-4,5-diol is synthesized by

[0074] (1) Preparation of 2-decyn-1-alcohol (compound 2 )

[0075] Add 50mL tetrahydrofuran, 5.32mL (90mmol) propynyl alcohol, 39.5mL (225mmol) hexamethylphosphoric triamide to a 250mL reaction flask successively under nitrogen protection, and slowly add 72mL (180mmol) n-butyl at -78°C Lithium solution. After 0.5 h of dropwise addition, the temperature was raised to -30°C and stirred for 3 h, and 7.07 mL (45 mmol) of n-bromoheptane was added, stirred for 20 min, then raised to room temperature and continued to react for 21 h. After the reaction was completed, 30 mL of saturated ammonium chloride aqueous solution was added, extracted with ether (30 mL'3), and the organic phases were combined. The organic phase was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was subjected to silica gel (200-300 mesh) column chromatogra...

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Abstract

The invention relates to a stereoselectivity complete synthesis method of panaxytriol. In the method, 5-bromine-1-pentene-4-alkyne-3-alcohol is taken as an intermediate, and a Cadiot-Chodkiewcz alkyne-alkyne coupling reaction is carried out on the intermediate and (4R, 5R)-1-dodecyne-4,5-glycol to synthesize the target product panaxytriol. The method provided by the invention has the advantages of simple and available reaction raw materials, short synthesis route, mild reaction conditions and high reaction overall yield.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry, and in particular relates to a synthesis method of panaxatriol. Background technique [0002] Natural polyynols mainly exist in plants such as Solanaceae, Platycodonaceae, Araliaceae, Pittogoniaceae, Oleaceae, Sandalaceae and Umbelliferae, and also have a certain distribution in Basidiomycetes. Studies have shown that polyacetylene alcohol compounds contained in ginseng have significant anti-inflammatory, anti-platelet aggregation, inhibition of cell oxidase, inhibition of leukemia cell growth, and inhibition of thrombosis. In addition, these polyacetylene alcohols extracted from Araliaceae It also has strong antitumor activity. Ginseng ( Panaxginseng C. A. Meyer.) is Araliaceae ( Araliaceae ) Panax ( Panax ) perennial herb whose root is a precious traditional medicine. Some studies have shown that ginseng contains many polyacetylene alcohol compounds, and these compounds have s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C33/048C07C29/34C07C33/044C07C29/36C07C33/42C07C27/02
Inventor 王博
Owner PAPANNA BEIJING TECH
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