22432-93-5

Usage

Uses

Used in Pharmaceutical Industry:
1,3,5-Triazin-2(1H)-one,4-amino-1-(3,5-di-O-acetyl-2-deoxy-D-erythro-pentofuranosyl)is used as a therapeutic agent for cancer and viral infections due to its ability to inhibit DNA and RNA replication.
Used in Scientific Research:
1,3,5-Triazin-2(1H)-one,4-amino-1-(3,5-di-O-acetyl-2-deoxy-D-erythro-pentofuranosyl)is used as an experimental tool in molecular biology for the study of nucleic acids, providing insights into their structure, function, and interactions with other molecules.
Used in Drug Development:
1,3,5-Triazin-2(1H)-one,4-amino-1-(3,5-di-O-acetyl-2-deoxy-D-erythro-pentofuranosyl)is used in the development of novel therapeutic agents targeting cancer and viral infections, leveraging its antitumor and antiviral properties to create more effective treatments.

Upstream product

• 30414-53-0 methyl propanoyl acetate 
• 52523-35-0 2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine 
• 151767-35-0 3,5-di-O-acetyl-2-deoxy-α/β-D-ribofuranoside 
• 4594-52-9 1,3,5-tri-O-acetyl-2-deoxyribose 

Downstream Products

• 2353-33-5 5-aza-2'-deoxycytidine 

Relevant academic research and scientific papers

Method for synthesizing decitabine key intermediate by solid acid catalysis

The invention belongs to the technical field of medicinal chemistry, and relates to a method for synthesizing a decitabine key intermediate (formula II) by solid acid catalysis. The method is characterized in that silicon dioxide loaded stannic chloride (SnCl4) is used as a catalyst for glycosylation reaction. The method has the advantages that the problem of complicated post treatment of a liquidacid catalyst is solved, and the content of beta-configuration intermediate can be effectively improved.

Method for synthesizing decitabine intermediate

The invention relates to a method for synthesizing a decitabine intermediate, in particular to a method for synthesizing the decitabine intermediate with a structure shown in a formula 2. According tothe method, the purity of the intermediate can be greatly improved, so that the purification operation of decitabine is reduced, a transition state intermediate compound is successfully separated forthe first time, and the total yield of decitabine is increased by three times.

Synthesis and properties of cross-linkable DNA duplex using 4-amino-2-oxo-6-vinyl-1,3,5-triazine

We synthesized the DNA oligonucleotide containing a new cross-linkable 4-amino-2-oxo-6-vinyltriazine (AOVT) nucleobase analogue (Et-AOVT) and evaluated these properties. Our results of the cross-link assay and thermal denaturing assay of duplexes containing AOVT demonstrated that the additional aza of AOVT has an impact on the duplex stability and crosslink properties. Our data suggests that the additional 5-aza of AOVT is involved in the hydrogen bonding with the complementary guanine, and this hydrogen bonding system successfully flipped the reactive vinyl group out to the major groove of the duplex demonstrating a new paradigm of a “cross-linkable duplex”.

Novel bi-cyclic or tri-cyclic heterocyclic compound

The present invention provides novel bi-cyclic or tri-cyclic compound represented by formula (I) or pharmaceutical acceptable salt thereof, [wherein, ring A is an aromatic group which may be substituted, one of X1 and X2 is a carbon atom, and another is a nitrogen atom, X3 is a nitrogen atom or CR2, X4 is a nitrogen atom or CR3, X5 is a sulfur atom or -CH=CH-, Z1 is an oxygen atom, -C(R6)(R7)-, -NH-, -C(R6)(R7)-NH-, -NH-C(R6)(R7)-, -C(R6)(R7)-O-, -O-C(R6)(R7)- or a single bone, one of Z2 and Z3 is CH and another one is a nitrogen atom, or both are nitrogen atoms, the other symbols are same as those defined in the specification.]

One-pot synthesis of 3,5-disubstituted and polysubstituted phenols from acyclic precursors

A new strategy for the synthesis of 3,5-disubstituted phenols is established through one-pot Robinson annulation of α,β-unsaturated ketones with α-fluoro-β-ketoesters followed by in situ dehydrofluorination and tautomerization. This method has been extended to the synthesis of polysubstituted phenols and applied in the preparation of biologically active compounds.

PREPARATION OF DECITABINE

The present application relates to processes for the preparation and purification of decitabine, and to processes for the preparation of a crystalline form of decitabine.

METHOD OF PURIFYING AND SEPARATING 2-FLUORO-3-OXOALKYLCARBOXYLIC ACID ESTER

The present invention concerns a method for purifying/separating a 2-fluoro-3-oxoalkylcarboxylic acid ester from a reaction mixture resulting from the fluorination of a 3-oxoalkylcarboxylic acid ester. The method involves depleting the reaction mixture of a hydrogen fluoride byproduct; and subsequently, separating the 2-fluoro-3-oxoalkylcarboxylic acid ester by distillation. The 2-fluoro-3-oxoalkylcarboxylic acid ester obtained by the method of the invention is highly pure and is thus suitable for use as an intermediate for the production of pharmacological products or agricultural chemicals.

Electrophilic fluorination with N,N′-difluoro-2,2′-bipyridinium salt and elemental fluorine

NNpm-Difluoro-22pm-bipyridiniu m bis(tetrafluoroborate) (MEC-31) was shown to be a highly reactive electrophilic fluorinating agent with the highest effective fluorine content in its class. We have developed the perfect recycled fluorination system with MEC-31 for the lower-cost industrial fluorination and for an environment. MEC-31 can be completely recycled including the counter-anion. We found the fluorination of 2-naphthol in liquid CO2 with MEC-31 in the presence of catalytic amount of NaOTf proceeded quantitatively without the generation of by-product. In the fluorination of 1,3-dicarbonyl compounds with elemental fluorine, we found the introduction method of fluorine gas would be very important in order to make a reaction efficient. As fluorination goes on, the quantity of 1,3-dicarbonyl compounds of the starting material is reduced gradually, and therefore the quantity of fluorine must be reduced by the method to control the flow rate or the concentration of fluorine gas diluted with nitrogen, together the fluorination to proceed efficiently.

PROCESS FOR PRODUCING 2-FLUORO-3-OXOALKYLCARBOXYLIC ACID ESTER

A process for producing a 2-fluoro-3-oxoalkylcarboxylic acid ester by fluorinating 3-oxoalkylcarboxylic acid ester with a fluorine gas is provided. The process is characterized in that the concentration of 3-oxoalkylcarboxylic acid ester in the reaction mixture for fluorination is maintained at 3wt% or higher. Also provided is a process for purifying 2-fluoro-3-oxoalkylcarboxylic acid ester characterized in that 2-fluoro-3-oxoalkylcarboxylic acid ester is produced at high yield and with less impurities by washing fluorinated 3-oxoalkylcarboxylic acid ester with 3 or more times as much water as the amount of reaction mixture. According to the processes of the present invention, not only is the generation of unwanted by-products minimized, but fluorinated 3-oxoalkylcarboxylic acid ester can be purified in an efficient manner. Thus, the present invention permits efficient production of considerably pure 2-fluoro-3-oxoalkylcarboxylic acid ester, a useful intermediate material in the production of various medical and agricultural agents.

High purity preparation of fluorinated 1,3-dicarbonyls using BDM (bis-fluoroxydifluoromethane)

A process for providing an α-fluorinated-β-dicarbonyl includes electrophilically fluorinating a β-dicarbonyl with bis-fluoroxydifluoromethane in the presence of an acid to provide the α-monofluorinated-β-dicarbonyl. The acid is preferably hydrofluoric acid. Preferred β-dicarbonyls include methyl-3-oxopentanoate and ethyl-4,4,4-trifluoroacetoacetate. The process can limit radical impurity byproducts to no more than 4% in some cases, and less than 0.5% in other cases. Theoretical yields of 95% α-monofluorinated-β-dicarbonyl are possible in some cases.