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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
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  • Abstract
  • Description
  • Claims
  • Application Information

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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

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  • 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

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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...

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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

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Application Information

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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
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