Method for preparing thioether-containing formyl sulpholipid conjugate

A technology containing thioether formyl thioester and formyl thioester, which is applied in the direction of organic chemistry, can solve the problems of large environmental pollution, highly toxic catalysts, and volatile toxicity of mercaptans, and achieves mild reaction conditions and cheap and easy reagents. The effect of easy separation and purification

Active Publication Date: 2019-09-20
LANZHOU UNIVERSITY
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Problems solved by technology

There are few studies on thioether and thioester conjugates. Among them, C.G.Kruse's group found that sulfolipids containing thioether bonds can be synthesized when studying 2-chlorotetrahydrofuran and 2-chlorotetrahydrothiophene. However, the yield of this method is low. Reaction processing is complex; Philip C. Bulman Page group in ZnCl via 2-acyl-1,3-dithiane 1-oxide 2 , under the condition of THF, thioether thioester compounds are obtained through rearrangement reaction, the substrate range is limited, and at the same time, this method uses a catalyst with high toxicity, which has a large environmental pollution
The preparation of conventional thioether compounds requires the use of thiol compounds. The volatility and toxicity of thiols increase the reaction operation and have a certain impact on the environment.

Method used

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  • Method for preparing thioether-containing formyl sulpholipid conjugate
  • Method for preparing thioether-containing formyl sulpholipid conjugate
  • Method for preparing thioether-containing formyl sulpholipid conjugate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012]

[0013] In a 10 ml round bottom flask, add 1,3-dithiane 2 (30 mg, 0.25 mmol), dissolve it with 2 ml of dichloromethane and add N-chlorosuccinimide (40 mg, 0.3 mmol), then Add FeCl 3 .6H 2 O (7mg, 0.025mmol), 1a (30mg, 0.21mmol), placed in air and stirred at room temperature for 3h. TLC detected that the reaction was stopped after the reaction was complete, and the product 3a was obtained by column chromatography after the solvent was evaporated. The resulting product data are characterized as follows: yellow oil; yield 89%; R f =0.18(EA / PE=1:10); 1 HNMR (300MHz, CDCl 3 )δ10.08(s,1H),7.42–7.15(m,5H),4.31(t,J=7.2Hz,1H),3.14–2.81(m,4H),2.51–2.25(m,2H),2.09 (s,3H),1.81–1.72(m,2H); 13 C NMR (75MHz, CDCl 3 )δ205.2, 187.4, 141.6, 128.6, 127.7, 127.4, 77.4, 77.0, 76.6, 49.9, 43.9, 30.7, 29.9, 28.7, 25.4; HRMS (ESI): m / z: calcd for C 14 h 19 o 2 S 2 [M+H] + :283.0826,found:283.0816.

Embodiment 2

[0015]

[0016] In a 10 ml round bottom flask, add 1,3-dithiane 2 (30 mg, 0.25 mmol), dissolve it with 2 ml of 1,2-dichloroethane and add N-chlorosuccinimide (40 mg, 0.3mmol), then add FeCl 3 .6H 2 O (7mg, 0.025mmol), 1b (34mg, 0.21mmol), placed in air and stirred at room temperature for 5h. TLC detected that the reaction was stopped after the reaction was complete, and the product 3b was obtained by column chromatography after the solvent was evaporated. The resulting product data are characterized as follows: yellow oil; yield 80%; R f =0.2(EA / PE=1:10); 1 HNMR (300MHz, CDCl 3 )δ10.08(s,1H),7.24–7.09(m,3H),7.06(s,1H),4.28(t,J=7.2Hz,1H),2.99–2.89(m,4H),2.42–2.29 (m,5H),2.10(s,3H),1.82–1.73(m,2H); 13 C NMR (75MHz, CDCl 3 )δ205.4, 187.5, 141.3, 138.2, 128.4, 128.2, 128.1, 124.6, 77.4, 77.0, 76.6, 49.8, 43.7, 30.7, 29.8, 28.6, 25.3, 21.4; HRMS (ESI): m / z: calcd for C 15 h 21 o 2 S 2 [M+H] + :297.0983,found:297.0980.

Embodiment 3

[0018]

[0019] In a 10 ml round bottom flask, add 1,3-dithiane 2 (30 mg, 0.25 mmol), dissolve it with 2 ml of dichloromethane and add N-chlorosuccinimide (40 mg, 0.3 mmol), then Add FeCl 3 .6H 2 O (7mg, 0.025mmol), 1c (38mg, 0.21mmol), placed in the air and stirred at room temperature for 8h. TLC detected that the reaction was stopped after the reaction was complete, and the product 3c was obtained by column chromatography after the solvent was evaporated. The resulting product data are characterized as follows: yellow oil; yield 83%; R f =0.11(EA / PE=1:10); 1 HNMR (300MHz, CDCl 3 )δ10.09(s,1H),7.29(d,J=0.9Hz,4H),4.30(t,J=7.2Hz,1H),3.05–2.89(m,4H),2.41–2.30(m,2H ),2.09(s,3H),1.83–1.73(m,2H); 13 C NMR (75MHz, CDCl 3 ))δ204.7, 187.2, 140.2, 133.0, 129.0, 128.7, 77.4, 77.0, 76.6, 49.8, 43.2, 30.6, 29.9, 28.7, 25.3; HRMS (ESI): m / z: calcd for C 14 h 18 ClO 2 S 2 [M+H] + :317.0437,found:317.0436.

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Abstract

The present invention relates to a method for preparing a thioether-containing formyl sulpholipid conjugate. The preparation method comprises: dissolving 1,3-dithiane and various unsaturated olefine ketones in an organic solvent in the presence of an activator N-chlorosuccinimide and a catalyst FeCl3.6H2O, carrying out a reaction for 2-8 h at a room temperature, and separating and purifying to obtain the thioether-containing formyl sulpholipid compound. According to the present invention, the method has characteristics of mild operating conditions, cheap and easily available substrate and simple reaction, and can be well used in the synthesis of pharmaceutical intermediates and biologically active conjugates.

Description

technical field [0001] The invention relates to a synthetic method for preparing thioether-containing formyl sulfide conjugates. Background technique [0002] Thioether and thiolipid compounds exist in large quantities in nature, and their special structure determines their good biological activity, and are widely used in medicine, chemistry, polymer and other fields. Thioether and thioester compounds are an important class of intermediates in organic chemistry, which can be used for the synthesis and transformation of various active substances, as well as for the construction of complex organic molecular skeletons and fragments, and can be applied to active pharmaceutical molecules and Synthesis of biological agents. There are few studies on thioether and thioester conjugates. Among them, C.G.Kruse's group found that sulfolipids containing thioether bonds can be synthesized when studying 2-chlorotetrahydrofuran and 2-chlorotetrahydrothiophene. However, the yield of this me...

Claims

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Application Information

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IPC IPC(8): C07C327/22
CPCC07C327/22C07C2601/08C07C2601/14
Inventor 张元闵灯刘剑
Owner LANZHOU UNIVERSITY
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