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Synthesis method for 4-S-5-Br-2',3',5'-O-triacetyluridine

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: 2019-08-09
DALIAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Synthesis method for 4-S-5-Br-2',3',5'-O-triacetyluridine
  • Synthesis method for 4-S-5-Br-2',3',5'-O-triacetyluridine
  • Synthesis method for 4-S-5-Br-2',3',5'-O-triacetyluridine

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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, Then adding different molar ratios of P 2 S 5 (0.391g, 1.76mmol) and Lawesson (0.356g, 0.88mmol) were used as vulcanizing agents, the reaction temperature was 95°C, the reaction was monitored by TLC, and the raw material point disappeared after 1.3h, which proved that the reaction was complete, and it was evaporated under reduced pressure at 55°C Solvent, the crude product is subjected to column separation (PE:EA=6:1; 4:1), after separation, it is mixed with absolute ethanol and petroleum ether for recrystallization, and the solid 4-S-5-Br-2' is obtained after suction filtration and drying ,3',5'-O-triacetyluridine 0.90g, the yield was 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, Then adding different molar ratios of P 2 S 5 (0.439g, 1.98mmol) and Lawesson (0.267g, 0.66mmol) were used as vulcanizing agents, the reaction temperature was 95°C, the reaction was monitored by TLC, and the raw material point disappeared after 1.3h, which proved that the reaction was complete, and it was evaporated under reduced pressure at 55°C Solvent, the crude product is subjected to column separation (PE:EA=6:1; 4:1), after separation, it is mixed with absolute ethanol and petroleum ether for recrystallization, and the solid 4-S-5-Br-2' is obtained after suction filtration and drying ,3',5'-O-triacetyluridine 0.92g, the yield was 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, Then adding different molar ratios of P 2 S 5 (0.488g, 2.2mmol) and Lawesson (0.178g, 0.44mmol) were used as vulcanizing agents, the reaction temperature was 95°C, the reaction was monitored by TLC, the raw material point disappeared after 1.3h, which proved that the reaction was complete, and it was evaporated under reduced pressure at 55°C Solvent, the crude product is subjected to column separation (PE:EA=6:1; 4:1), after separation, it is mixed with absolute ethanol and petroleum ether for recrystallization, and the solid 4-S-5-Br-2' is obtained after suction filtration and drying ,3',5'-O-triacetyluridine 0.93g, the yield was 91%.

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Abstract

The invention belongs to the field of chemical synthesis and discloses a synthesis method for 4-S-5-Br-2',3',5'-O-triacetyluridine. The synthesis method comprises the steps that a compound 5-Br-2',3',5'-O-triacetyluridine serves as a raw material, phosphorus pentasulfide and a Lawesson reagent are combined to serve as a vulcanization reagent, 1,4-dioxane serves as a solvent, and a chemical reaction is carried out to finally prepare the 4-S-5-Br-2',3',5'-O-triacetyluridine. The synthesis method for the 4-S-5-Br-2',3',5'-O-triacetyluridine has the advantages that the reaction time is shortened,and the vulcanization efficiency is greatly improved. The synthesis method reduces the cost, the treatment after the reaction is simple and convenient, and meanwhile the yield of the thionucleoside compound after the reaction is increased.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and the invention relates to a method for synthesizing 4-S-5-Br-2', 3', 5'-O-triacetyluridine from a sulfurized amide. Background technique [0002] During the long development 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 for treating cancer include: radiotherapy; chemotherapy; surgical treatment; ultraviolet light and nucleoside therapy. Photochemotherapy, in which ultraviolet radiation (UVR: 280-400nm) or visible light photosensitive drugs are combined to produce a therapeutic effect [2] , which neither drugs nor radiation alone can achieve, is a well-established non-malignant proliferative treatment for skin conditions and various cancers. [0003] According to a large number of recent studies, sugar- and base-modified nucleoside compounds exhibit good antitumor activity, and 4-thionucleo...

Claims

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Application Information

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Patent Type & Authority Applications(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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