Method for synthesizing 4-S-2', 3', 5'-O-triacetyluridine

A technology of triacetyl uridine and 4-S-2, which is applied in chemical instruments and methods, bulk chemical production, sugar derivatives, etc., and can solve the problems of phosphorus pentasulfide being highly toxic, long reaction time, perishable price, etc. , to achieve the effect of simple and convenient post-reaction treatment, easy operation, and improved vulcanization efficiency

Active Publication Date: 2019-09-06
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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  • Method for synthesizing 4-S-2', 3', 5'-O-triacetyluridine
  • Method for synthesizing 4-S-2', 3', 5'-O-triacetyluridine
  • Method for synthesizing 4-S-2', 3', 5'-O-triacetyluridine

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Embodiment 1

[0039] Dissolve 2',3',5'-O-triacetyluridine (1.00g, 2.70mmol) in 50mL of 1,4-dioxane, stir to fully dissolve, then add different molar ratios P 2 S 5 (0.479g, 2.16mmol) and Lawesson (0.436g, 1.08mmol) were used as vulcanizing agents, heated to 95°C for reaction, and the reaction was monitored by TLC. The disappearance of the raw material point in 20min proved that the reaction was complete, and the solvent was evaporated under reduced pressure at 55°C , the crude product is subjected to column separation (PE:EA=6:1; 4:1), after separation, it is recrystallized by mixing absolute ethanol and petroleum ether, and the solid 4-S-2',3',5 '-O-triacetyluridine 0.938g, the yield is 90%.

Embodiment 2

[0041] Dissolve 2',3',5'-O-triacetyluridine (1.00g, 2.70mmol) in 50mL of 1,4-dioxane, stir to fully dissolve, then add different molar ratios P 2 S 5 (0.539g, 2.43mmol) and Lawesson (0.327g, 0.810mmol) were used as vulcanizing agents, heated to 95°C to react, and the reaction was monitored by TLC. The raw material point disappeared after 20min, which proved that the reaction was complete, and the solvent was evaporated under reduced pressure at 55°C , the crude product is subjected to column separation (PE:EA=6:1; 4:1), after separation, it is recrystallized by mixing absolute ethanol and petroleum ether, and the solid 4-S-2',3',5 '-O-triacetyluridine 0.969g, the yield is 93%.

Embodiment 3

[0043] Dissolve 2',3',5'-O-triacetyluridine (1.00g, 2.70mmol) in 50mL of 1,4-dioxane, stir to fully dissolve, then add different molar ratios P 2 S 5 (0.599g, 2.70mmol) and Lawesson (0.218g, 0.540mmol) were used as vulcanizing agents, heated to 95°C to react, and the reaction was monitored by TLC. The raw material point disappeared after 20min, which proved that the reaction was complete, and the solvent was evaporated under reduced pressure at 55°C , the crude product is subjected to column separation (PE:EA=6:1; 4:1), after separation, it is recrystallized by mixing absolute ethanol and petroleum ether, and the solid 4-S-2',3',5 '-O-triacetyluridine 1.001g, the yield is 96%.

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Abstract

The invention belongs to the field of chemical synthesis, and discloses a method for synthesizing 4-S-2', 3', 5'-O-triacetyluridine. According to the synthesis method, a compound 2', 3', 5'-O-triacetyluridine is used as a raw material, phosphorus pentasulfide and a Lawesson's reagent are combined to be used as a vulcanizing agent, 1,4-dioxane is used as a solvent for chemical reaction, and finally4-S-2', 3', 5'-O-triacetyluridine is prepared. By the method for synthesizing 4-S-2', 3', 5'-O-triacetyluridine provided by the invention, the reaction time is shortened, and moreover, the vulcanization efficiency is greatly improved. According to the synthesis method provided by the invention, the cost is reduced, the reaction aftertreatment is simple and convenient, and meanwhile, the yield ofa reaction thionucleoside compound is improved.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and the invention relates to a method for synthesizing 4-S-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-thionucleoside ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H19/09C07H1/00C07H1/06
CPCC07H19/09C07H1/00C07H1/06Y02P20/55
Inventor 张晓辉武文慧
Owner DALIAN UNIV
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