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

Synthesis of rhodiola glycoside compound

A technology of salidroside and its synthesis method, which is applied in chemical instruments and methods, sugar derivatives, sugar derivatives, etc., can solve the problems of expensive silver carbonate, uneconomical synthesis method, unsuitable for industrial production, etc., and achieve the goal of producing The effect of high rate and simple method

Inactive Publication Date: 2003-03-19
上海药谷药业有限公司
View PDF0 Cites 7 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This technology makes it easy-to-use but produces very good results with less effort compared to traditional methods like chemical or physical processes used by other industries such as pharmaceutical companies.

Problems solved by technology

This patented technical problem addressed in this patents relates to finding an economically viable way to produce high purity saltedrosides that have certain beneficial properties such as antioxygen activity or fatigue resistance without having excessive use of costly materials like Silver Carbonate.

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] 2,3,4,6-O-tetrabenzoyl-α-D-glucosyl trichloroacetimidate (18.5 g, 25 mmol) and 4-acetoxyphenethyl alcohol (3.6 g, 20 mmol mol) was dissolved in anhydrous dichloromethane (100 ml), 4A molecular sieves (5 g) were added, cooled to -40°C, boron trifluoride diethyl ether (0.18 ml) was added dropwise, after the addition was complete, it was stirred at room temperature After 30 minutes, triethylamine (0.2 ml) was added to quench the reaction, filtered, and the filtrate was concentrated and separated by column chromatography. The eluent was petroleum ether:ethyl acetate=6:1-4:1, and 14.5 g of syrup was obtained. The solid is (4-acetoxyphenethyl)-β-D-2,3,4,6-O-tetrabenzoylglucopyranoside, and the yield is 96%. 1 HNMR (300MHz, CDCl 3 ): 8.1-7.2(m, 20H), 7.07(d, 2H, J=8.1Hz), 6.73(d, 2H, J=8.1Hz), 5.89(t, 1H, J=9.8Hz), 5.67(t , 1H, J=9.6Hz), 5.54(dd, 1H, J=9.6, 9.8Hz), 4.38(d, 1H, J=9.8Hz), 4.64(dd, 1H, J=3.0, 12.3Hz), 4.50 (dd, 1H, J=8.1, 12.0Hz), 4.13(m, 2H), 3.72(m, 1H), 2.8...

Embodiment 2

[0022] 2,3,4,6-O-Tetraacetyl-α-D-glucosyl trichloroacetimidate (2.25 g, 4.6 mmol) and 4-acetoxyphenethyl alcohol (0.66 g, 3.65 mmol ) was dissolved in anhydrous dichloromethane (30 ml), 4A molecular sieves (1 g) were added, cooled to -78°C, trimethylsilyl trifluoromethanesulfonate (0.03 ml) was added dropwise, after the addition was complete, Rise to room temperature and stir for 30 minutes, add water (0.1 ml) to quench the reaction, filter, concentrate the filtrate, and separate by column chromatography, the eluent is petroleum ether: ethyl acetate: dichloromethane = 6: 1: 1-4 : 1: 1, 1.65 grams of syrupy solids were obtained, which was (4-acetoxyphenethyl)-β-D-2,3,4,6-O-tetraacetylglucopyranoside, and the yield was 89% . 1 HNMR (300MHz, CDCl 3 ): 7.18(d, 2H, J=8.1Hz), 7.00(d, 2H, J=8.1Hz), 5.19(t, 1H, J=9.8Hz), 5.09(t, 1H, J=9.8Hz), 4.99(t, 1H, J=9.8Hz), 4.48(d, 1H, J=9.8Hz), 4.26(dd, 1H, J=3.0, 12.3Hz), 4.13(dd, 1H, J=8.1, 12.0Hz ), 3.83(t, 1H, J=6.6Hz), 3.65(m, 2H), 2....

Embodiment 3

[0024] (4-Acetoxyphenethyl)-β-D-2,3,4,6-O-tetrabenzoylglucopyranoside (13.8 g, 18 mmol) was dissolved in methanol and dichloromethane Add sodium methoxide (50%, 3.24 g, 30 mmol) to the mixed solvent (100 ml, 1:1), stir at room temperature for 4 hours, add strong acid resin to neutralize to pH 6, filter, and wash the resin with methanol , after concentration, column chromatography, the eluent was chloroform:methanol=4:1, and 5.5 g of salidroside was obtained with a yield of 100%. The nuclear magnetic resonance, infrared spectrum, ultraviolet spectrum, mass spectrum, specific rotation and melting point are all consistent with the literature values.

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 present invention relates to the synthesis of rhodiola glycoside compound. Under the catalyst of boron trifluoride etherate, trifluoromethyl sulfonic acid, trialkylsilyl triflate, perchloric acid or other Lewis acid, 1-glycoimino ester and substituted phenyl ethanol as raw material react to produce polysubstituted rhodiola glycoside compound; and the polysubstituted rhodiola glycoside compound is reacted with hydroxide, carbonate or methoxide to produce rhodiola glycoside compound. The said process is simple, high in yield and suitable for industrial production.

Description

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

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
Owner 上海药谷药业有限公司
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