Unlock instant, AI-driven research and patent intelligence for your innovation.

The preparation method of steroid compound

A steroid compound and compound technology are applied in the field of preparation of steroid compounds, which can solve the problem of no reports on the total synthesis of natural products, and achieve the effects of being convenient for research and use and increasing sources.

Active Publication Date: 2020-01-07
SOUTH UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, so far there is no report on the total synthesis of such natural products

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
  • The preparation method of steroid compound
  • The preparation method of steroid compound
  • The preparation method of steroid compound

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0026] The preparation method of the steroidal compound of one embodiment is used for preparing the steroidal compound cyclocitrinol, and the method comprises the following steps:

[0027] Step S110: Under the conditions of anhydrous and -78°C, the structural formula is Compound A reacts with lithium diisopropylamide in the first organic solvent for 0.5 hours to 4 hours, and then adds trimethylchlorosilane to continue the reaction to obtain the compound containing the structural formula: The first crude product of Compound B.

[0028] Among them, the molar ratio of compound A to lithium diisopropylamide is 1:1 to 1:2.5, the molar ratio of compound A to trimethylchlorosilane is 1:1 to 1:2, Me is methyl, and TMS is Trimethylsilyl.

[0029] Specifically, in the step of adding trimethylchlorosilane to continue the reaction, thin-layer chromatography is used to detect whether the reaction is complete. The time for adding trimethylchlorosilane to continue the reaction is 1 hour...

Embodiment 1

[0112] The steps of the preparation method of the steroid compound of the present embodiment are as follows:

[0113] (1) Dissolve compound A (20.0g, 78.6mmol) in anhydrous tetrahydrofuran (300mL) at -78°C to obtain a tetrahydrofuran solution of compound A; at -78°C, under continuous stirring, the The tetrahydrofuran solution of compound A was added in lithium diisopropylamide (47.2mL, 2.0mol / L), and the reaction was stirred at this temperature for half an hour, then trimethylchlorosilane (7.5mL, 86.5mmol) was added, and the Continue to stir the reaction at high temperature, and use a thin-layer chromatographic plate to detect until the reaction is complete. For about 1 hour, quench the reaction with saturated ammonium chloride solution, dilute and extract the reaction solution with ether, and use saturated ammonium chloride and saturated saline for the organic phase in turn. Wash, then dry and filter with anhydrous sodium sulfate, spin dry the organic solvent under reduced pr...

Embodiment 2

[0157] The steps of the preparation method of the steroid compound of the present embodiment are as follows:

[0158] (1) Dissolve Compound A (20.0g, 78.6mmol) in anhydrous ether (300mL) at -78°C to obtain an ether solution of Compound A; at -78°C, under continuous stirring, the The ether solution of compound A was added in lithium diisopropylamide (98.25mL, 2.0mol / L), and the reaction was stirred at this temperature for 4 hours, and then trimethylchlorosilane (13.63mL, 157.2mmol) was added. Continue to stir the reaction under temperature, and detect with thin-layer chromatographic plate until the reaction is complete, about 2 hours, quench the reaction with saturated ammonium chloride solution, dilute and extract the reaction solution with diethyl ether, after the aqueous phase is extracted with diethyl ether twice, the combined organic phase, and the organic phase was washed successively with saturated ammonium chloride and saturated brine, then dried and filtered with anhyd...

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 preparation method of a steroidal compound. According to the preparation method of the steroidal compound, a compound A with a structural formula as shown in the specification is used as a starting raw material, a type II[5+2] reaction is taken as a key reaction, so as to construct a large-tension [4,4,1] double-ring framework with bridgehead double bond rapidly and efficiently, a carbon-oxygen dual bond is cut off through a lithium-ethylamine condition, oxidation and formaldehyde elimination are performed by using potassium tert-butoxide under the aerobic conditionso as to obtain alkone, and finally, a lithium reagent is used for addition to introduce a side chain so as to prepare the steroidal compound cyclocitrinol. The steroidal compound with a structural formula as shown in the specification is prepared through a chemical synthesis method, so that the source of the steroidal compound is increased so as to be convenient to research and use.

Description

technical field [0001] The invention relates to a preparation method of a steroid compound. Background technique [0002] Cyclocitrinol is a natural product isolated from the sponge penicillium citrinum by Kozlovsky et al. in 2000. It is a new class of steroidal compounds. Its correct structure was deduced by Philip Crews group in 2003 through the X-ray single crystal diffraction structure of its family analogues. So far more than 20 families of natural products have been isolated and identified. The natural products of the cyclocitrinols family have unique chemical structure characteristics: they have a common [7-7-6-5] tetracyclic core skeleton, in which the A / B ring system is a bicyclic [4.4.1] bridged ring system with high tension; There is a bridgehead double bond in the A ring, which has great ring tension and is a great challenge in the total synthesis. At the same time, multiple compounds in the cyclocitrinol family of natural products exhibited special biological...

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 Patents(China)
IPC IPC(8): C07J67/00
CPCC07J67/00
Inventor 刘君羊吴建磊范建红李闯创
Owner SOUTH UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA