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Process of stereospecific synthesis of sapogenins

A kind of technology of aglycone and saponin, applied in the field of stereospecific synthesis of saponin, can solve problems such as difficult separation

Inactive Publication Date: 2008-06-11
PHYTOPHARM LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This mixture is reported to be difficult to separate

Method used

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  • Process of stereospecific synthesis of sapogenins
  • Process of stereospecific synthesis of sapogenins
  • Process of stereospecific synthesis of sapogenins

Examples

Experimental program
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preparation example Construction

[0049] In the reaction step of preparing the required saponin in the first aspect of the present invention, as the starting material of this step, 3-ketone, 5β-H steroidal saponin is preferably except for 3- All positions other than the position group are consistent with all positions of the required saponin. However, if necessary or desired, appropriate protecting groups can be used for reduction and then removed to obtain the desired saponin.

[0050] The term "protecting group" as used herein refers to a group used to protect reactive functional groups such as hydroxyl or carboxyl groups to avoid unnecessary participation in the reaction when they are desired groups in the final product. Conventional protecting groups can be used according to standard practice, and specific examples can be found in T.W. Green and P.G.M. Wuts in "Protective Groups in Organic Chemistry" John Wiley and Sons, 1991; J.F.W McOmie in "Protective Groups in Organic Chemistry" Plenum Press, 1973.

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Embodiment 1

[0088] Synthesis of smilagenin from smilagenone with L-Selectride® at -10°C

[0089] Smilax saponinone (657 g) was dissolved in tetrahydrofuran (4000 ml), the solution was purged with nitrogen, and the solution was cooled until the internal temperature reached about -10°C. To the solution was added L-Selectride(R) (1 M in THF, 2400 mL) over about 50 minutes and stirred for 90 minutes. A solution of citric acid (600 g) in water (2000 ml) was added slowly, keeping the temperature below 0°C. The mixture was warmed to room temperature and stirred for 30 minutes. The aqueous layer was separated and extracted with dichloromethane (2000ml) and the layers were separated. The aqueous layer was extracted with dichloromethane (1500ml). The combined organic extracts were washed with water (4000ml) and washed with MgSO 4 dry. Evaporate the organic extract to obtain the different smilax saponin.

Embodiment 2

[0091] Synthesis of smilagenin from smilagenone with K-Selectride® at -15°C

[0092] To a solution of smilaxaponinone (500 g) in tetrahydrofuran (3500 ml) was added K-Selectride(R) (1600 ml, 1M in THF) under a nitrogen atmosphere at a temperature of about -15°C. The reaction mixture was stirred at this temperature for 30 minutes. Quench with aqueous citric acid (393 g citric acid dissolved in 1300 ml water), keeping the internal temperature around 0°C. The mixture was warmed to room temperature and the THF was evaporated at atmospheric pressure until a solid precipitated. The solid was filtered and pumped dry.

[0093] The solid was dissolved in dichloromethane (DCM) (6000ml), dried (MgSO 4 ) and evaporated to give a white solid which was recrystallized in isopropanol (IPA) (5000ml) to give smilaxa saponin.

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Abstract

The present invention relates to a stereotactic synthesis method of saponins. The method is to convert 3α-hydroxyl-5β-H steroidal saponins and derivatives thereof into 3β-hydroxyl-5β-H steroidal saponins A method for ligands and derivatives thereof, comprising: making the 3- The hydroxyl-activated derivative is contacted with a nucleophile and optionally subsequent adjustments to the 3-position substituent are made as desired. The present invention provides a simple route to obtain useful steroidal saponins, such as smilax saponin, from readily available or easily prepared starting materials (such as diosgenin ketone prepared from diosgenin) Agenin, epismilagenin, isosmilagenin, epiisosmilagenin and esters thereof.

Description

[0001] This application is a divisional application, the international application number of the original application is PCT / GB2003 / 001780, the international application date is April 28, 2003, the Chinese national application number is 03824744.5, and the date of entry into China is April 28, 2005 , the title of the invention is "Stereospecific Reduction Method of Saponin-3-one". technical field [0002] The present invention relates to the stereospecific synthesis method of saponin. Background technique [0003] It has been pointed out that certain saponins and their derivatives (more specifically, saponins containing 5β hydrogen atoms, especially compounds containing 3-hydroxyl and 5β hydrogen atoms, such as sarsaparilla saponins Sarsasapogenin, episarsasapogenin, smilagenin and epismilagenin are useful in the treatment of cognitive impairment and other diseases. The description of this activity is referred to, for example, WO 99 / 48482, WO99 / 48507, WO 01 / 49703, WO 02 / 079...

Claims

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Application Information

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IPC IPC(8): C07J71/00
Inventor 菲利普·詹姆斯·冈宁彼得·戴维·蒂芬
Owner PHYTOPHARM LTD
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