143157-25-9

Basic information

• Product Name: 2-Deoxy-2,2-difluoro-D-ribose-3,5-dibenzoate
• Synonyms: 2-Deoxy-2,2-difluoro-3,5-bisbenzolyloxy-D-riboflouranose;2-Deoxy-2,2-difluoro-D-ribose-3,5-dibenzoate
• CAS NO: 143157-25-9
• Molecular Formula: C19H16F2O6
• Molecular Weight: 378.3235464
• Mol File: 143157-25-9.mol

Chemical Properties

• Boiling Point: 495.925 °C at 760 mmHg
• Flash Point: 253.726 °C
• Appearance: /
• Density: 1.412 g/cm³
• PKA: 9.95±0.70(Predicted)
• CAS DataBase Reference: 2-Deoxy-2,2-difluoro-D-ribose-3,5-dibenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Deoxy-2,2-difluoro-D-ribose-3,5-dibenzoate(143157-25-9)
• EPA Substance Registry System: 2-Deoxy-2,2-difluoro-D-ribose-3,5-dibenzoate(143157-25-9)

Safety Data

• Hazardous Substances Data: 143157-25-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-Deoxy-2,2-difluoro-D-ribose-3,5-dibenzoate is used as a building block in organic synthesis for the creation of new molecules with potential applications in various industries. Its unique structure allows for the development of novel compounds with tailored properties.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 2-Deoxy-2,2-difluoro-D-ribose-3,5-dibenzoate is utilized as a key component in the design and synthesis of pharmaceutical agents. Its distinctive properties contribute to the discovery of new drugs with improved efficacy and selectivity.
Used in Drug Discovery:
2-Deoxy-2,2-difluoro-D-ribose-3,5-dibenzoate serves as a valuable tool in drug discovery, aiding researchers in identifying and optimizing lead compounds with therapeutic potential. Its unique structural features facilitate the exploration of new chemical space and the development of innovative therapeutic agents.
Used in Chemical Biology:
In chemical biology, 2-Deoxy-2,2-difluoro-D-ribose-3,5-dibenzoate is employed to study the interactions between small molecules and biological targets. Its distinctive properties enable the investigation of novel biological pathways and the development of probes for understanding complex biological processes.
Overall, 2-Deoxy-2,2-difluoro-D-ribose-3,5-dibenzoate is a versatile compound with a wide range of applications across various scientific disciplines, particularly in the development of new pharmaceutical agents and the advancement of our understanding of biological systems.

Upstream product

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Relevant articles and documents

High-selectivity synthesis method for gemcitabine intermediate

The invention discloses a high-selectivity synthesis method for a gemcitabine intermediate. The high-selectivity synthesis method specifically comprises the following process: Step 1, synthesis of T1;Step2, synthesis of T2, to be specific, 550kg of hydrogen peroxide is dropwise added into the T1, and a reaction is controlled to produce the T2; Step3, synthesis of T3, to be specific, sodium acetate trihydrate or sodium carbonate is added into a reaction kettle, the PH value is adjusted with glacial acetic acid, a 10%-15% sodium hypochlorite aqueous solution is dropwise added, and a reaction iscontrolled to produce the T3; Step 4, synthesis of T4; Step 5, synthesis of T5; Step 6, synthesis of T6; Step 7, synthesis of T7; Step 8, synthesis of T8; and Step9, T8 configuration transformation.The high-selectivity synthetic method for the gemcitabine intermediate can reduce the production cost, and meanwhile, can also increase the yield of the gemcitabine intermediate.

Purification method of gemcitabine intermediate

The invention provides a purification method of a gemcitabine intermediate, and belongs to the technical field of drug intermediate synthesis. According to the invention, a compound 2 in an existing method (shown in a formula 1 and a formula 2 in a background art) is reduced to obtain a mixture containing a compound 3 and a byproduct compound 9; the mixture reacts with aniline; dehydration condensation reaction of the compound 3 and aniline is achieved; Schiff base is generated; the Schiff base and the byproduct compound 9 are easy to separate; a high-purity compound 3 can be obtained by performing simple acidic hydrolysis and separation on the separated Schiff base; the high-purity compound 3 is subjected to sulfonylation reaction to synthesize a gemcitabine hydrochloride key intermediate compound 5, so that the yield and the purity of the compound 5 can be improved, and the preparation yield and the product quality of the raw material medicine gemcitabine hydrochloride are ensured.

Method for recovering mother liquor of gemcitabine intermediate

The invention provides a method for recovering mother liquor of a gemcitabine intermediate, and relates to the technical field of purification. The method for recovering the mother liquor of the gemcitabine intermediate provided by the invention comprises the following steps of: performing acidolysis of crystallization mother liquor containing a compound 5 and a compound 10 so as to obtain a mixture of a compound 3 and a compound 9; mixing the mixture of the compound 3 and the compound 9 with aniline, and performing dehydration reaction to obtain a mixture of Schiff base 12 and the compound 9; performing separation of the mixture of the Schiff base 12 and the compound 9 to obtain high-purity Schiff base 12; performing hydrolysis of the high-purity Schiff base 12 to obtain the compound 3; and mixing the compound 3 with methylsulfonyl chloride, and performing acylation reaction so as to obtain the high-purity compound 5. The method provided by the invention can remove the compound 10 in the crystallization mother liquor to obtain the high-purity compound 5, so that the yield and the purity of hydrochloride, namely gemcitabine hydrochloride, are improved.

Stereoselective N-glycosylation with N4-acyl cytosines and efficient synthesis of gemcitabine

Through systematical comparison of various N4-protected cytosine derivatives in the glycosylation step of gemcitabine synthesis, highly beta-stereoselective and high yielding TBAI catalyzed N-glycosylation was achieved with N4-Bz cytosine and anomeric mixture of 2,2‘-difluororibose mesylate donor. The subsequent global deprotection gave gemcitabine efficiently. Meanwhile, the anomeric chloride intermediate and fluoride-displaced side products of this N-glycosylation were identified, too. This new glycosylation method reveals the importance of N4-protection in the stereoselective preparation of pyrimidine nucleoside, also provides a potential alternative to current industrial process to gemcitabine.

Preparation method of cytidine

The invention provides a preparation method of cytidine 1, which comprises the following steps: (1) carrying out a condensation reaction on a compound 6 and a compound 7 in the presence of stannic chloride to generate a compound 8; (2) removing an alpha-isomer and other reaction impurities in the compound 8 to obtain the beta-isomer compound 8; and (3) carrying out a deprotection reaction on the beta-isomer compound 8 in the presence of an alcohol solvent, and then carrying out a salt forming reaction with hydrochloric acid to obtain a compound 1. The nucleoside compound 8 can be obtained withhigh beta-stereoselectivity starting from a cheap raw material 7 with a mixed anomeric carbon configuration, especially the raw material 7a, and a slightly excessive basic group 6, especially the basic group 6a; the trace alpha-compound 8 isomer impurities can be removed from the nucleoside compound 8 through a simple pulping method; and subsequently, deprotection and salifying reactions for beta-compound 8 have high yield, so that the method can reduce the production cost of the compound 1.

Preparation method of gemcitabine intermediate methylsulfonyl ester

The invention relates to a preparation method of a gemcitabine intermediate methylsulfonyl ester, and belongs to the technical field of drug intermediate synthesis. In order to solve the problems of low conversion rate and large amount of waste liquid in the prior art, the preparation method of the gemcitabine intermediate methylsulfonyl ester is provided. The method comprises the step that in a mixed solvent of a water-insoluble organic solvent and catalytic amount isopropyl alcohol, a compound 2-deoxy-2,2-difluoro-D-erythro-1-furazolidone-3,5-dibenzoyl ester in formula I is subjected to a reduction reaction to be converted into a compound in formula II in the coexistence of aluminum isopropoxide and sodium tert-butoxide; cooling is carried out to control the temperature of a reaction liquid to be lower than 5 DEG C, methylsufonyl chloride is added to perform an esterification reaction, and the corresponding compound gemcitabine intermediate methylsulfonyl ester in formula III is obtained. The preparation method of the gemcitabine intermediate methylsulfonyl ester can effectively increase the reaction speed and conversion rate, reduces the generation of impurities, has higher yield and purity requirements, can achieve a one-pot reaction, and simplifies the production operation.

Preparation method of 2-deoxy-2, 2-difluoro-D-red-3, 5-dibenzoate

The invention relates to a preparation method of 2-deoxy-2, 2-difluoro-D-red-3, 5-dibenzoate and belongs to the technical field of medicine intermediate synthesis. In order to solve the problems of poor selectivity and safety in the prior art, the inventi

Industrial preparation process for key intermediate sulfonated saccharide of Gemcitabine

The invention relates to a preparation method for a compound represented by a formula (I) shown in the description, i.e., a key intermediate sulfonated saccharide of Gemcitabine. The final product is prepared through subjecting a compound represented by a formula (II) shown in the description to sodium borohydride reduction, hydroxyl protection and resolution. The method is simple in process, high in yield and high in product purity and has no need of harsh reaction conditions, thereby being very suitable for industrial production.

Azido nucleosides and nucleotide analogs

Disclosed herein are 4′-azido-substituted nucleosides, nucleotides and analogs thereof, pharmaceutical compositions that include one or more of 4′-azido-substituted nucleosides, nucleotides and analogs thereof, and methods of synthesizing the same. Also disclosed herein are methods of ameliorating and/or treating a disease and/or a condition, including an infection from a paramyxovirus and/or an orthomyxovirus, with a 4′-azido-substituted nucleoside, a nucleotide and/or an analog thereof. Examples of viral infections include a respiratory syncytial viral (RSV) and influenza infection.

Thiophene-expanded guanosine analogues of Gemcitabine

The chemotherapeutic drug Gemcitabine, 2′,2′-difluoro-2′-deoxycytidine, has long been the standard of care for a number of cancers. Gemcitabine's chemotherapeutic properties stem from its 2′,2′-difluoro-2′-deoxyribose sugar, which mimics the natural nucleoside, but also disrupts nucleic acid synthesis, leading to cell death. As a result, numerous analogues have been prepared to further explore the biological implications for this structural modification. In that regard, a thieno-expanded guanosine analogue was of interest due to biological activity previously observed for the tricyclic heterobase scaffold. Several analogues were prepared, including the McGuigan ProTide, however the parent nucleoside exhibited the best chemotherapeutic activity, specifically against breast cancer cell lines (89.53% growth inhibition).