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Synthetic method of rhodiola rosea active ingredient rosavin or rosarin

A technology of active ingredients and synthesis methods, applied in the field of compound synthesis, can solve the problems of no application prospect, unsatisfactory overall yield, heavy metal residues, etc., and achieve the solution of unstable yield, good industrialization prospects, and mild reaction conditions Effect

Inactive Publication Date: 2019-12-20
天圆(宁波)生物医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method does not have the phenomenon of low yield and instability in the preparation of disaccharide donors, but because the linear synthesis method is still used, the overall yield is still not ideal, and the Mizoroki-Heck reaction requires the use of palladium catalysts, and the cost is relatively high. High, and there is the possibility of heavy metal residues, therefore, this synthesis strategy does not have application prospects in the preparation of rosavin and rosarin in large quantities

Method used

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  • Synthetic method of rhodiola rosea active ingredient rosavin or rosarin
  • Synthetic method of rhodiola rosea active ingredient rosavin or rosarin
  • Synthetic method of rhodiola rosea active ingredient rosavin or rosarin

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038]

[0039]Stir 50g of L-arabinose in 800mL of pyridine, gradually add 270g of acetic anhydride, the system gradually turns light yellow and transparent, then stir and react overnight at room temperature, add 100mL of methanol to quench the reaction after the reaction, and then spin off the system solvent , the remaining oil was dissolved with 500ml of dichloromethane, washed successively with 200mL of 1M hydrochloric acid and 200mL of saturated sodium bicarbonate, then the organic phase was collected and dried over anhydrous sodium sulfate. After drying, the solvent was spun off to obtain 126g of yellow oil, namely Dissolve fully acetylated arabinose in 300mL of dichloromethane, add 42g of thiophenol and 55g of 47% boron trifluoride ether solution in turn, and stir the system at room temperature overnight. After the reaction, add 50g of triethylamine After the reaction was quenched, the system solvent was spun off, and the remaining oil was subjected to rapid silica gel...

Embodiment 2

[0042]

[0043] Dissolve 50g of fully acetylated arabinose in 200mL of dichloromethane, then add 32g of iodine and 21g of hexamethyldisilazane (HMDS), stir at room temperature for 3 hours, and add 13g of dimethyl disulfide after the conversion is complete. The system was stirred and reacted overnight at room temperature. After the reaction was completed, the system was concentrated and purified on a silica gel column to obtain 42 g of a light yellow oily substance, sugar donor A2, with a yield of 87%.

[0044] 1 H NMR (400MHz, CDCl 3 )δ5.56(d,J=2.0Hz,1H),5.31(s,1H),5.25–5.30(m,1H),5.10–5.15(m,1H),4.53–4.37(m,1H),4.15 –4.33(m,1H),2.15(s,3H),1.90–2.10(m,9H).

Embodiment 3

[0046]

[0047] Dissolve 50g of fully acetylated arabinose in 100mL of 37% hydrogen bromide acetic acid solution, stir the system at room temperature overnight, then spin off the solvent, dissolve the remaining oil in 500mL of dichloromethane, and then add saturated sodium bicarbonate The pH of the system was adjusted to neutral with the solution, and then the organic phase was collected and dried over anhydrous sodium sulfate. After drying, the solvent was spun off to obtain 38 g of a slightly yellow oily substance, ie sugar donor A3, with a yield of 71%.

[0048] 1 H NMR (400MHz, CDCl 3 )δ6.62(m,1H),5.38–5.41(m,1H),4.96–5.05(m,1H),4.05–4.15(m,2H),3.53–3.90(m,1H),2.01–2.15( m, 9H).

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Abstract

The present invention provides a synthetic method of rhodiola rosea active ingredient rosavin or rosarin. A convergent synthetic strategy is adopted, rosin is used as a starting material and modifiedinto sugar acceptors through protection and deprotection strategies, then sugar acceptors and sugar donors formed by arabinopyranose and arabinyl furanose in presence of an accelerator quickly and efficiently conduct synthesis of rosavin and rosarin. The related synthetic method is cheap and easy-to-obtain in raw materials and mild in reaction conditions, the obtained product is high in purity, and compared with currently reported linear synthesis strategy, the method has very good industrialization prospects.

Description

technical field [0001] The invention belongs to the technical field of compound synthesis, and in particular relates to a method for synthesizing rosevin or loxaline, an active ingredient of rhodiola rosea. Background technique [0002] Rhodiola rosea is a traditional precious Chinese medicinal material belonging to the genus Rhodiola (Crassulaceae) of the sedum family (Crassulaceae). Its roots and stems are often used as medicinal parts. At present, there are about 96 varieties of Rhodiola, most of which are distributed in alpine regions, such as the Himalayas, East Asia, West Asia and North America; there are about 73 varieties of Rhodiola in my country, most of which are in the northeast of China , North China, Southwest and Northwest, etc., mostly in Tibet, Sichuan and Yunnan high-altitude cold regions, the most important varieties are: Rhodiola daflora, Rhodiola narrow-leaf, Rhodiola kuye, Rhodiola rosea and Rhodiola Hima, etc. . At present, Rhodiola extracts are mainly...

Claims

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Application Information

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IPC IPC(8): C07H15/18C07H1/00
CPCC07H1/00C07H15/18Y02P20/55
Inventor 苗志伟钱金金蔡岩孙波钱怡赵佩佩
Owner 天圆(宁波)生物医药科技有限公司
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