Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Synthetic method of 20(R)-ginsenoside Rh2

A synthetic method, ginsenoside technology, applied in the field of synthesis of rare ginsenosides, can solve problems such as difficult to increase yield, cumbersome reaction steps, large loss of raw materials, etc., and achieve low cost, simple synthetic route and high selectivity

Inactive Publication Date: 2012-10-17
上海兰蒂斯生物医药科技有限公司
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The initial raw material of this method is also protopanaxadiol group saponin, and reaction step is loaded down with trivial details, and raw material loss is bigger, thereby causes cost increase, is difficult to improve yield, and what obtain after hydrolysis is the mixed saponin of (R&S) configuration

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Synthetic method of 20(R)-ginsenoside Rh2
  • Synthetic method of 20(R)-ginsenoside Rh2
  • Synthetic method of 20(R)-ginsenoside Rh2

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Example 1: Synthesis of 12-substituted protopanaxadiol (a2)

[0020] (1) Synthesis of 12-acetyl-20(R)-protopanaxadiol (that is, R1 is acetyl)

[0021] 20(R)-Protopanaxadiol (a1) (self-made) 4.6g (0.01mol) was dissolved in pyridine (50ml), acetic anhydride 1.5g (0.015mol) was added at room temperature, stirred overnight at 25°C, LC-MS showed After the reaction was complete, 50 ml of ice water was added to quench the reaction, concentrated under reduced pressure, the aqueous phase was extracted with ethyl acetate, washed with saturated brine until neutral, and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the crude product was subjected to silica gel column chromatography (eluent: volume ratio of petroleum ether to ethyl acetate 4:1) to obtain 4.3 g of compound (a2) with a yield of 85.1% and a HPLC purity of 93.2%.

[0022] (2) Synthesis of 12-acetyl panaxadiol (that is, R1 is acetyl)

[0023] Panaxadiol (b1) (self-made) 4.6g (0.01mol)...

Embodiment 2

[0024] Embodiment 2: glycosylation reaction

[0025] (1) 500mg (0.001mol) of compound (a2) and compound c1 (prepared according to the method of Shenyang Pharmaceutical University Journal 2005 / 22 / 05, R2 is acetyl) 590mg (0.0012mol) were dissolved in 10ml of anhydrous dichloromethane Add 200 mg of 4A molecular sieves, stir at room temperature for 0.5 hours, add 100 mg of Amberlyst 15, and react with stirring at 20°C for 2 hours. After the reaction was completed, the filtrate was concentrated, and the 200-300 mesh silica gel column chromatography, eluent: the volume ratio of sherwood oil and ethyl acetate was 2: 1, to obtain 700 mg of compound (a3), with a yield of 82%, and the purity determined by HPLC was 92.13%.

[0026] (2) 500mg (0.001mol) of compound (b2) and compound c1 (prepared according to the method of Shenyang Pharmaceutical University Journal 2005 / 22 / 05, R2 is acetyl) 590mg (0.0012mol) were dissolved in 10ml of anhydrous dichloromethane , add 200 mg of 4A molecular...

Embodiment 3

[0027] Embodiment 3: deprotection group reaction

[0028] (1) Dissolve 830 mg (0.001 mol) of compound (a3) ​​in 10 ml of methanol, add 680 mg (0.01 mol) of sodium ethoxide in batches under stirring, react at 50° C. for 8 hours, and the reaction is complete. The reaction solution was concentrated to obtain a white solid, which was recrystallized from acetonitrile to obtain 510 mg of compound (a4) with a yield of 83.89% and a purity of 99% as determined by HPLC.

[0029] (2) 830 mg (0.001 mol) of compound (b3) was dissolved in 10 ml of methanol, and 560 mg (0.01 mol) of potassium hydroxide was added in batches under stirring, and reacted at 50° C. for 8 hours, and the reaction was completed. The reaction solution was concentrated to obtain a white solid, which was recrystallized from acetonitrile to obtain 480 mg of compound (a4) with a yield of 82.01% and a purity of 99.2% as determined by HPLC.

[0030] Compound (a4) was tested by TLC, LC-MS, 1 H-NMR, 13 C-NMR, IR, 13 C- ...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to a synthetic method of 20(R)-ginsenoside Rh2, comprising the following steps of: firstly protecting 20(R)-protopanaxadiol or panaxadiol to obtain 12-substituted 20(R)-protopanaxadiol or 12-substituted panaxadiol, performing glycosylation of substituted 20(R)-protopanaxadiol or substituted panaxadiol and glucosyl donor in the presence of a molecular sieve and an acid catalyst, removing protective groups, separating and purifying to obtain 20(R)-ginsenoside Rh2. The method provided by the invention has advantages of mild reaction condition and low cost; and the reaction product obtained by the method has high stereoselectivity, high yield and high purity, and is suitable for industrial production.

Description

technical field [0001] The present invention relates to a synthetic method of rare ginsenosides with biological activity, specifically: 20(R)-ginsenoside Rh2, i.e. 20(R)-protopanaxadiol-3-O-β-D-glucoside The synthetic method of pyranoside, whose structure is shown below. [0002] Background technique [0003] In recent years, a large number of studies have been carried out on the efficacy of ginsenoside monomers at home and abroad, revealing that the strength of its anti-tumor activity is as follows: protopanaxadiol type > protopanaxatriol type, aglycon > monoglycoside > diglycoside > three Glycosides>tetraglycosides, 20(R)-ginsenosides>20(S)-ginsenosides. Due to the low sugar chain saponins and aglycon components in plants, the preparation work of low sugar chain saponins such as ginsenoside Rh2 and Rg3 in plants of the genus Panax has received special attention, and wherein ginsenoside Rg3 has been used as a class of new drugs (see one Capsule) has b...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07J17/00
CPCY02P20/55
Inventor 栾德刚邙志国蒋爱芳栾松平
Owner 上海兰蒂斯生物医药科技有限公司
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com