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

Complete E/F ring-opening synthesis process of 26-chloro-3beta, 16beta-diacetyloxy-22-one-(5-) cholestane (cholestene) with sterioside

A technology of diacetoxy and steroidal saponins, applied in steroids, organic chemistry and other directions, can solve problems such as low yield, and achieve the effects of high atom utilization and simple steps

Inactive Publication Date: 2007-12-19
YUNNAN UNIV
View PDF0 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] The ring-opened product of this method not only retains the complete carbon skeleton, but also 16 、C 22 、C 26 The corresponding functional group has also been introduced, but due to the multi-step process, the yield is low

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
  • Complete E/F ring-opening synthesis process of 26-chloro-3beta, 16beta-diacetyloxy-22-one-(5-) cholestane (cholestene) with sterioside
  • Complete E/F ring-opening synthesis process of 26-chloro-3beta, 16beta-diacetyloxy-22-one-(5-) cholestane (cholestene) with sterioside
  • Complete E/F ring-opening synthesis process of 26-chloro-3beta, 16beta-diacetyloxy-22-one-(5-) cholestane (cholestene) with sterioside

Examples

Experimental program
Comparison scheme
Effect test

Embodiment Construction

[0030] 1: Acetylation of Diosgenin and Sisalogenin

[0031] General method:

[0032] Put 1 mol of diosgenin (sisalgenin) in a 1000mL reaction bottle, add ethyl acetate with a mass of about 3 to 5 times as a solvent and about 5% mol of diosgenin (sisalin) as a catalyst , stir and slowly add 1.1 mol of acetic anhydride as esterification agent at room temperature, and then reflux for about 8-9 hours after the addition of acetic anhydride is completed. After the reaction is detected by TLC, pour the reaction mixture into another container and add an appropriate amount of NaHCO 3 Saturated solution, adjust the pH value to about 6-7, separate the ethyl acetate phase, extract the water phase twice with an appropriate amount of ethyl acetate, combine the organic phases, wash the organic phase once with saturated saline, and dry over anhydrous sodium sulfate. The solid residue obtained after stripping the solvent was purified by recrystallization from methanol.

[0033] Acetyldiosge...

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 complete sterioside E / F ring-opening process for synthesizing 26-chloro-3beta, 16beta-diacetyl oxy-22-one-(5-) cholestane (cholestene) belongs to the field of organic synthesis technology. The process includes the first C3-OH acetylation of the material, cheap yamogenin or sisal sapogenin, to obtain acetylated sapogenin; the subsequent selective complete E / F ring-opening of the acetylated sapogenin in acetic anhydride solution at 80 deg.c via introducing dry hydrogen chloride gas to obtain coarse product; and final purification via silica gel column chromatography to obtain the product. The present invention has cheap material, simple operation, easy separation and purification of the product and high yield.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis. Background technique [0002] Steroidal saponins are a class of oligoglycosides that use sterol compounds with 27 carbon atoms as aglycones to combine with oligosaccharides. They are widely distributed in nature, mainly concentrated in plants such as Liliaceae, Dioscoreaceae and Agaveaceae, and most concentrated in the genus Dioscorea and Liliaceae. [0003] Among the numerous steroidal sapogenins, the ones with the most industrial application value are diosgenin obtained from yam, sisal sapogenin obtained from sisal, and sapogenin obtained from tomato. [0004] Since the 1960s, the degradation products of steroidal saponins have been playing a huge role in the synthesis of steroidal hormone drugs and steroidal contraceptives. In the 1990s, with the development of steroidal saponin chemistry, many new biologically active saponins It was gradually discovered, especially the effects of ...

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
IPC IPC(8): C07J9/00
Inventor 朱洪友雷泽戴佶程水连付正启木晓云温晓江
Owner YUNNAN UNIV
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