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Synthesis method of dendriform compound trifluoroacetate using cage-type octamer (gamma-aminopropyl)silsesquioxane as core

A technology of trifluoroacetate and silsesquioxane, which is applied in the field of synthesis of dendrimer trifluoroacetate (G3(OL) trifluoroacetate), achieves less pollution, less species and higher yield high effect

Inactive Publication Date: 2013-04-24
NINGBO INST OF TECH ZHEJIANG UNIV ZHEJIANG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method has three condensation and three deprotection steps, and each condensation step requires a 3.75-fold excess of HOBt, HBTU, and lysine dicyclohexylamine salt relative to the number of amino groups on the starting material, and these excess compounds can cause severe environmental pollution; in addition, this method not only has a long reaction time, and each step of the reaction needs about two days (48 hours), and in the post-processing step, when the reaction mixture is added to the aqueous citric acid solution, a thick paste will be formed. The paste cannot be filtered, and the water-soluble impurities wrapped in it must be repeatedly diffused and washed for at least 6 times for 5 hours each time to be basically removed
This situation leads to a long and cumbersome post-processing process
And the overall yield of the reaction is not high, only 8.23%

Method used

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  • Synthesis method of dendriform compound trifluoroacetate using cage-type octamer (gamma-aminopropyl)silsesquioxane as core
  • Synthesis method of dendriform compound trifluoroacetate using cage-type octamer (gamma-aminopropyl)silsesquioxane as core

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] 1. Dissolve OAS hydrochloride (0.50g, 0.43mmol) and DIPEA (0.89g, 6.88mmol) in 20ml DMF, stir for 30min, then add N,N'-di-tert-butoxy in 30ml DMF drop by drop Carbonyl-L-lysine N-succinimide ester (3.05g, 6.88mmol), stirred at room temperature for 12 hours. After the reaction was completed, 150ml of acetonitrile chilled to 0°C was added, filtered, and the resulting solid was vacuum-dried at room temperature for 24 hours to obtain tert-butoxycarbonyl-protected G1(OL) (1.21g, 0.34mmol), with a yield of 80%.

[0024] 2. Add tert-butoxycarbonyl-protected G1(OL) (1.02g, 0.29mmol) into trifluoroacetic acid (5ml) chilled to 0°C and stir for 4 hours. After the reaction was completed, the reaction mixture was added to 50 ml of diethyl ether cooled to 0°C, and the precipitate was collected by filtration to obtain 0.80 g (0.21 mmol) of G1(OL) trifluoroacetate, with a yield of 74%.

[0025] 3. Using G1(OL) trifluoroacetate as raw material, adjust the molar ratio of G1(OL), DIPEA a...

Embodiment 2

[0028]1. Dissolve OAS hydrochloride (0.50g, 0.43mmol) and DIPEA (0.89g, 6.88mmol) in 20ml DMF, stir for 30min, then add N,N'-di-tert-butoxy in 30ml DMF drop by drop Carbonyl-L-lysine pentafluorophenol ester (3.52g, 6.88mmol), stirred and reacted at room temperature for 8 hours. After the reaction was completed, 150ml of acetonitrile chilled to 0°C was added, filtered, and the resulting solid was vacuum-dried to obtain tert-butoxycarbonyl-protected G1(OL) (1.28g, 0.37mmol), with a yield of 85%.

[0029] 2. Add tert-butoxycarbonyl-protected G1(OL) (1.02g, 0.29mmol) into trifluoroacetic acid (5ml) chilled to 0°C and stir for 4 hours. After the reaction was completed, the reaction mixture was added to 50 ml of diethyl ether cooled to 0°C, and the precipitate was collected by filtration to obtain 0.86 g (0.23 mmol) of G1(OL) trifluoroacetate, with a yield of 80%.

[0030] 3. Using G1(OL) trifluoroacetate as raw material, the molar ratio of G1(OL) trifluoroacetate, DIPEA and N,N-di...

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Abstract

The invention discloses a method for synthesizing dendriform compound trifluoroacetate using cage-type octamer (gamma-aminopropyl)silsesquioxane as a core, which comprises the following steps: dissolving OAS hydrochloride and DIPEA (diisopropylethylamine) in DMF (N,N-dimethylformamide), dropwisely adding N,N'-di-tert-butoxycarbonyl-L-lysine N-succinimide ester or N,N'-di-tert-butoxycarbonyl-L-lysine penta-fluorophenol ester dissolved in DMF, and reacting for 10-14 hours; adding -2-2 DEG C acetonitrile, filtering, and drying for 20-24 hours to obtain tert-butoxycarbonyl-protected G1(OL); adding the G1(OL) into -2-2 DEG C trifluoroacetic acid to react for 3-5 hours, adding the reaction mixture into -2-5 DEG C aether, mixing, standing, filtering, and collecting the precipitate, thereby obtaining G1(OL) trifluoroacetate; and adjusting the proportion of the reaction materials, and repeating the rest of steps to obtain G3(OL) trifluoroacetate. The invention has the advantages of low pollution, short reaction time, simple after-treatment and high yield.

Description

technical field [0001] The invention relates to a method for synthesizing a dendrimer trifluoroacetate (G3(OL) trifluoroacetate) with a cage octamer (γ-aminopropyl) silsesquioxane as the core. Background technique [0002] Organic molecules with a dendritic structure are called dendrimers. Dendrimers generally consist of a core at the center of the molecule and monomers extending outward from the core. Depending on the number of layers of repeating monomers, one generation, two generation up to n generation dendrimers can be formed. like figure 1 As shown, the nucleus (G0) of this dendrimer has three layers of repeated monomers on the periphery, so it is a three-generation dendrimer (G3 for short). [0003] Dendritic compounds are widely used and can be used as catalysts, carriers of drugs or medical contrast agents, etc. Common dendrimers include porphyrin dendrimers, aryl ether dendrimers, polyamide-amine dendrimers (PAMAM), ferrocenyl dendrimers, etc. Cage octameri...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G83/00
Inventor 骆成才胡桂香沈银周赛春
Owner NINGBO INST OF TECH ZHEJIANG UNIV ZHEJIANG
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