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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: 2010-08-11
YUNNAN UNIV
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

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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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 The invention belongs to the technical field of organic synthesis. Background technique 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. 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. 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 preventing and treating cardiova...

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Application Information

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Patent Type & Authority Patents(China)
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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