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Synthetic method of spirosolane glycoalkaloids

A kind of technology of spiro alkane and synthesis method, which is applied in the field of drug synthesis and can solve the problems of low efficiency and the like

Active Publication Date: 2013-07-10
OCEAN UNIV OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The use of heavy metal silver salts (such as silver triflate) as accelerators for the glycosylation reaction and the adoption of inefficient step-by-step synthesis strategies are disadvantages of these methods.

Method used

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  • Synthetic method of spirosolane glycoalkaloids
  • Synthetic method of spirosolane glycoalkaloids
  • Synthetic method of spirosolane glycoalkaloids

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Embodiment Construction

[0077] The present invention will be described in detail below with reference to the accompanying drawings and specific examples of solamargine and solasodine, but the present invention is not limited to the following content.

[0078] Preparation and data of compound 2

[0079] Diosgenin 1 (3.0g, 4.60mmol), dichloromethane (30mL), glacial acetic acid (3.3mL, 32.2mmol) were added successively in a single-necked bottle, and under argon protection, the After stirring in ice bath for 20min, slowly add BF dropwise 3 ·OEt 2 , the dropwise addition was completed within 25 minutes, the reaction product was immediately transferred to ice water, stirred to make it fully mixed; then extracted with dichloromethane, collected and combined the organic phase, then washed with saturated sodium bicarbonate and saturated brine, and washed with anhydrous sulfuric acid Sodium was dried and filtered, and the filtrate was concentrated and then silica gel column chromatography (CH 2 Cl 2 : ethy...

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Abstract

The invention discloses a convergent chemical synthetic method of spirosolane glycoalkaloids. The method comprises the following steps of: (a) converting silica or acyl-protected spirostanol saponin (II) for 3-hydroxy into corresponding 16-acetoxyl group-22-carbonyl-26-N-hydroxy-cholesterol (III); (b) preparing silica or acyl-protected 16-acetoxyl group-22-carbonyl-26-N-sulfonic acid ester cholesterol (IV) for 3-hydroxy; (3) preparing silica or acyl-protected 16-acetoxyl group-22-carbonyl-26-azido cholestane (V) for 3-hydroxy; (d) preparing spirosolane sapogenin (VI); (e) preparing acyl-protected spirosolane glycoalkaloids (VII), and (f) preparing the spirosolane glycoalkaloids (I). The preparation method disclosed by the invention is simple in technology, high in yield, and strong in practical value.

Description

technical field [0001] The invention belongs to the field of drug synthesis, and relates to a convergent chemical synthesis method of spirostanoid alkaloids. technical background [0002] Spirostaline-type glycoalkaloids are an important class of plant secondary metabolites, mainly distributed in plants of the genus Solanum and Tomato in the family Solanaceae, such as nightshade, eggplant, tomato and potato. Spirosteroidalkane-type glycoalkaloids consist of a C with an oxygen-azaspirodecane E / F ring 27 Spirostaline alkane saponins (such as Australian solanamine, tomato amine and tomato enamine, etc.) and oligosaccharide chains (such as potato triose, solanitriose, etc.). Solanine, solanine and tomatine are typical representatives of spirostanoid alkane glycoalkaloids (Lee, K.-R.; Kozukue, N.; Han, J.-S.; Park, J. -H.; Chang, E.-Y.; Baek, E.-J.; Friedman, M.J. Agric. Food Chem. 2004, 52, 2832-2839). [0003] Solanine and solanine isolated from Solunum sodomaeum are effecti...

Claims

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Application Information

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IPC IPC(8): C07J71/00
CPCY02P20/55
Inventor 李明王鹏彭雁南陈朋伟
Owner OCEAN UNIV OF CHINA
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