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Synthetic method of pterostilbene

The technology of pterostilbene and compound is applied in the synthesis field of phytoestrogen pterostilbene, can solve the problems of low yield, high price, poor stereoselectivity and the like, and achieves the effects of high stereoselectivity, simple process and mild reaction conditions

Inactive Publication Date: 2007-05-02
NAN JING RHINE PHARM TECH
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0005] Marinella Roberti et al. (J.Med.Chem.46:3546-3554, 2003) reported for the first time to prepare triphenylphosphonium bromide salt with 3,5-dimethoxybenzyl bromide and triphenylphosphine. The 4'-hydroxyl of p-hydroxybenzaldehyde is protected by dimethyl chloride silicon (TBDMS), carries out Wittig (Wittig) reaction, removes protecting group again and obtains pterostilbene, but yield is low, and stereoselectivity is poor; And tert Butyldimethylsilyl chloride is unstable, which brings difficulties in use and storage, and the price is relatively expensive, which makes the cost of pterostilbene rise

Method used

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Experimental program
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Embodiment 1

[0019] Step A: Dissolve 11.7g (0.11mol) of p-hydroxybenzaldehyde in 100ml of dichloromethane, add 17.4ml (0.33mol) of N,N-diisopropylethylamine, then add dropwise 18.8ml of chloromethyl methyl ether ( 0.22mol), refluxed for 3.5 hours, evaporated the solvent, added 200ml of ethyl acetate and 200ml of water. Ethyl acetate was fractionated three times, washed with saturated NaCl, dried, and the solvent was evaporated to obtain crude methoxybenzaldehyde, which was used in the next reaction.

[0020] Step B: Add 21.8 g (0.11 mol) of 3,5-dimethoxybenzyl chloride and 39 g (0.24 mol) of triethyl phosphite into the reactor, keep the reaction at 140°C for 5 hours, and vacuum the excess at 105°C The triethyl phosphite was distilled off. Add dry DMF120ml, then add 12.5950% sodium methoxide under cooling, react at 5°C for 2 hours until dissolved, then add p-methoxymethoxybenzaldehyde into the reactor, react at room temperature for 2 hours, heat up to 100°C, gradually Cool down to room te...

Embodiment 2

[0023] Step A: Use 16.3g (0.12mol) of p-hydroxybenzyl alcohol and 15.2g (0.12mol) of benzyl chloride to condense into ether, then feed chlorine gas to obtain 23.4g (0.1mol) of 4'-benzyloxybenzyl chloride, add 39g (0.24mol) of triethyl phosphite was reacted at 140°C for 6 hours; 120ml of DMF and 12.5g of 50% sodium methoxide were added under cooling and reacted at 5°C for 2 hours until dissolved.

[0024] Step B: Add 17.4 g (0.1 mol) of 3,5-dimethoxybenzaldehyde to the above solution, react at room temperature for 1.5 hours, then raise the temperature to 100°C for 1.5 hours, and react at room temperature for 10 hours to obtain benzyl ether The compound crude product 33g was directly used in the next reaction.

[0025] Step C: Add 100ml of N,N-dimethylaniline and 33ml of dichloromethane to the above benzyl ether compound, stir at 0°C for 10 minutes, add 40g of anhydrous aluminum chloride, react for 6 hours, add 1.0M hydrochloric acid 20ml, stirred, the mixture was extracted wit...

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Abstract

This invention relates to a composing preparation of pterostilbene, this preparation uses 3,5-dipl-methoxyl Chlorobenzyl and P-hydroxy benzaldehyde or uses 3,5-dipl-methoxybenzaldehyde and p-hydroxyl group alcohol benzyl (first protected, second chlorinated), by method of protecting 4'-hydroxy group and producing phosphonate agentia, carry out Wittig-Horner reaction, then pterostilbene is produced by hydrolization and schizolysis.

Description

field of invention [0001] The invention relates to the field of organic chemistry, in particular, the invention relates to a synthesis method of phytoestrogen pterostilbene. Background technique [0002] Pterostilbene (Pterostilene), CAS: [537-42-8], also known as dimethyl ether resveratrol. [0003] Pterostilbene is an active natural compound extracted from various plants including dracaena and grape. Medical research has continuously found that pterostilbene not only has antioxidant properties, can remove free radicals in the body, but also has strong anti-inflammatory and anti-tumor effects, and is also the precursor of resveratrol with multi-functional health care effects. [0004] Lu Wenjie et al. (Acta Pharmaceutica Sinica 33:755-758, 1998) reported the extraction of pterostilbene from the wood of Dracaena saponifera; [0005] Marinella Roberti et al. (J.Med.Chem.46:3546-3554, 2003) reported for the first time to prepare triphenylphosphonium bromide salt with 3,5-dim...

Claims

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Application Information

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IPC IPC(8): C07C41/30C07C43/205C07C43/215C07C43/23
Inventor 陈新梅以成
Owner NAN JING RHINE PHARM TECH
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