129664-48-8

Upstream product

• 3601-90-9 5-chloro-2-(((4-chlorobenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-chlorobenzoate 
• 7057-43-4 5-trifluoromethyl-2,4-bis(trimethylsilyloxy)pyrimidine 
• 21740-23-8 3,5-O-bis(4-chlorobenzoyl)-2-deoxy-α-D-ribofuranosyl chloride 

Relevant academic research and scientific papers

Synthesis of trifluorothymidine: Green glycosylation condition using neither chloroform nor transition metals

A new green glycosylation condition useful for efficient large-scale preparation of trifluorothymidine 1 is described. The condition requires neither CHCl3 nor transition-metal catalysts for β-selectivity at the anomeric C1-position, which is advantageous for process development of active pharmaceutical ingredients such as 1. Key features of the condition include: (1) only an equimolar amount of trifluorothymine 2 is required, (2) the glycosylation is performed under high concentration, (3) the reaction is carried out at 50 °C to enhance the reaction.

Method for synthesizing trifluridine process impurity

The invention discloses a method for synthesizing a trifluridine impurity 1-((2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione, and belongs tothe technical field of chemical pharmacy. The method comprises the following steps: condensing starting raw materials 5-trifluoromethyl-2,4-bis(trimethylsilyloxy)uracil (2) and 1-chloro-2-deoxy-3,5-di-4-chlorobenzoyl-D-ribose (3) to prepare 3',5'-di(4-chlorobenzoyl)-2'-deoxy-alpha-D-ribose-5-trifluoromethyluracil (4); and hydrolyzing the compound (4) to generate 1-((2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione (1). The highly-pure trifluridine impurity synthesized in the invention can be used as an impurity standard product in the detection and analysis of finished trifluridine, so the accurate localization and qualitative diagnosis of the impurity in the detection and analysis of the finished trifluridine are improved, and theenhancement of the control of the impurity is benefited, thereby the quality of the finished trifluridine is improved. The method has the advantages of cheap and easily available raw materials, and simplicity in operation, and allows the yield of the obtained product to be (40 +/- 5)% and the HPLC purity of the product to be equal to or more than 98%.

THE SYNTHESIS OF 2'-DEOXY-5-TRIFLUOROMETHYLURIDINE UTILIZING A COUPLING REACTION

The coupling reaction between 1-α-chloro-2-deoxyribose derivative and silylated 5-trifluoromethyluracil was examined.The best stereoselectivity was obtained when the reaction was carried out using a large amount of silylated base in the presence of anhydrous zinc chloride.