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A kind of 4-s-5-br-2', 3', 5'-o-triacetyl uridine synthesis method

A 4-s-5-br-2, triacetyl uridine technology, applied in chemical instruments and methods, bulk chemical production, sugar derivatives, etc. Long time and other problems, to achieve the effect of simple and convenient post-reaction treatment, improved vulcanization efficiency, and easy operation

Active Publication Date: 2022-07-12
DALIAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As we all know, phosphorus pentasulfide has been widely used in various types of vulcanization reactions, but phosphorus pentasulfide is highly toxic, and it is easy to generate flammable gas of hydrogen sulfide when it meets water, and the reaction time is too long for the experimental reaction; The storage conditions are also strict, perishable and expensive, and for experimental reactions, the time is long and the yield is low

Method used

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  • A kind of 4-s-5-br-2', 3', 5'-o-triacetyl uridine synthesis method
  • A kind of 4-s-5-br-2', 3', 5'-o-triacetyl uridine synthesis method
  • A kind of 4-s-5-br-2', 3', 5'-o-triacetyl uridine synthesis method

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Experimental program
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Effect test

Embodiment 1

[0043] Dissolve 5-Br-2',3',5'-O-triacetyluridine (1.00g, 2.20mmol) in 50mL of 1,4-dioxane, stir at room temperature to fully dissolve, Subsequently, different molar ratios of P were added 2 S 5 (0.391g, 1.76mmol) and Lawesson (0.356g, 0.88mmol) as vulcanizing agent, the reaction temperature was 95°C, the reaction was monitored by TLC, the starting point disappeared in 1.3h, which proved that the reaction was complete, and steamed under reduced pressure at 55°C Solvent, the crude product was subjected to column separation (PE:EA=6:1; 4:1), after separation, mixed with absolute ethanol and petroleum ether for recrystallization, suction filtration and drying to obtain solid 4-S-5-Br-2' ,3',5'-O-triacetyluridine 0.90g, the yield is 88%.

Embodiment 2

[0045] Dissolve 5-Br-2',3',5'-O-triacetyluridine (1.00g, 2.20mmol) in 50mL of 1,4-dioxane, stir at room temperature to fully dissolve, Subsequently, different molar ratios of P were added 2 S 5 (0.439g, 1.98mmol) and Lawesson (0.267g, 0.66mmol) as vulcanizing agents, the reaction temperature was 95°C, the reaction was monitored by TLC, the starting point disappeared in 1.3h, which proved that the reaction was complete, and steamed under reduced pressure at 55°C Solvent, the crude product was subjected to column separation (PE:EA=6:1; 4:1), after separation, mixed with absolute ethanol and petroleum ether for recrystallization, suction filtration and drying to obtain solid 4-S-5-Br-2' ,3',5'-O-triacetyluridine 0.92g, the yield is 90%.

Embodiment 3

[0047] Dissolve 5-Br-2',3',5'-O-triacetyluridine (1.00g, 2.20mmol) in 50mL of 1,4-dioxane, stir at room temperature to fully dissolve, Subsequently, different molar ratios of P were added 2 S 5 (0.488g, 2.2mmol) and Lawesson (0.178g, 0.44mmol) as vulcanizing agents, the reaction temperature was 95°C, the reaction was monitored by TLC, the raw material point disappeared in 1.3h, which proved that the reaction was complete, steamed out under reduced pressure at 55°C Solvent, the crude product was subjected to column separation (PE:EA=6:1; 4:1), after separation, mixed with absolute ethanol and petroleum ether for recrystallization, suction filtration and drying to obtain solid 4-S-5-Br-2' ,3',5'-O-triacetyluridine 0.93g, the yield is 91%.

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Abstract

The invention belongs to the field of chemical synthesis and discloses a method for synthesizing 4-S-5-Br-2', 3', 5'-O-triacetyluridine. The synthesis method uses compounds 5-Br-2', 3', 5'-O-triacetyluridine as raw materials, phosphorus pentasulfide and Lawesson's reagent are combined as sulfurization reagents, and 1,4-dioxane is used as solvent A chemical reaction occurs to finally prepare 4-S-5-Br-2', 3', 5'-O-triacetyluridine; 4-S-5-Br-2', 3', 5'-O-triacetyl uridine provided by the invention, The method for synthesizing 5'-O-triacetyluridine not only shortens the reaction time, but also greatly improves the vulcanization efficiency. The synthesis method provided by the invention reduces the cost, the post-reaction treatment is simple and convenient, and the yield of the reacted thionucleoside compounds is improved.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and relates to a method for synthesizing 4-S-5-Br-2', 3', 5'-O-triacetyluridine by sulfide amide. Background technique [0002] In the long development process of life research, the research on cancer has always been the focus of people's attention. The main cause of cancer is DNA damage [1] . The methods of treating cancer include: radiotherapy; chemotherapy; surgery; ultraviolet light and nucleoside therapy. Photochemotherapy, where ultraviolet radiation (UVR: 280-400nm) or visible light photosensitive drugs are combined to produce a therapeutic effect [2] Neither drugs nor radiation alone can be achieved, and is a proven non-malignant proliferative treatment for skin conditions and various cancers. [0003] According to a large number of recent studies, nucleoside compounds modified by sugar and base show good antitumor activity, and 4-thionucleoside analogs are used as antiviral [3] , a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H19/067C07H1/00C07H1/06
CPCC07H19/067C07H1/00C07H1/06Y02P20/55
Inventor 张晓辉武文慧
Owner DALIAN UNIV
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