95058-77-8

Usage

Uses

Used in Pharmaceutical Industry:
2-Deoxy-2,2-difluoro-D-threo-pentonic acid γ-lactone is utilized as a potential therapeutic agent for the treatment of diabetes and metabolic disorders due to its ability to inhibit key enzymes involved in carbohydrate metabolism. This action may help regulate blood sugar levels and improve overall metabolic health in patients.
Used in Medicinal Chemistry Research:
In the realm of medicinal chemistry, 2-Deoxy-2,2-difluoro-D-threo-pentonic acid γ-lactone serves as a subject of interest for the development of novel compounds with enhanced inhibitory properties. Its unique structure allows researchers to explore its potential in creating new drugs that can effectively target and modulate enzyme activities related to metabolic pathways.
Used in Synthetic Organic Chemistry Research:
2-Deoxy-2,2-difluoro-D-threo-pentonic acid γ-lactone is also employed in synthetic organic chemistry as a building block or a starting material for the synthesis of complex organic molecules. Its distinctive fluorinated structure offers opportunities for the creation of new chemical entities with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.

Upstream product

• 69602-83-1 C₁₃H₁₂O₆ 
• 928797-50-6 ethyl (3R,S)-2,2-difluoro-3-hydroxy-(2,2-dimethyldioxolpent-4-yl)propionate 
• 95058-92-7 (erytro) ethyl-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-difluoro-3-hydroxy propionate 
• 76-05-1 trifluoroacetic acid 
• 114420-06-3 ethyl 2-deoxy-2,2-difluoro-D-erythro,D-threo-pentonate 
• 95058-92-7 ethyl 2,2-difluoro-3(R)-hydroxy-3-(2,2-dimethyl-1,3-dioxolan-4-yl)propionate 
• 667-27-6 Ethyl bromodifluoroacetate 
• 132850-49-8 3-(R)-1,4-Dioxa-spiro[4.5]dec-2-yl-2,2-difluoro-3-triethylsilanyloxy-propionic acid ethyl ester 

Downstream Products

• 924264-45-9 3,5-bis(tert-butyl-diphenylsilyloxy)-2-deoxy-2,2-difluoro-1-oxoribose 
• 1147119-07-0 (3R,4R)-5-trityloxy-3-hydroxy-2,2-difluoro-pentanoic acid γ-lactone 
• 1147119-13-8 (2R,3R)-4,4-difluoro-5-(methylsulfonyloxy)-2-(trityloxymethyl)tetrahydrofuran-3-yl benzoate 
• 1147119-14-9 (2R,3R)-4,4-difluoro-5-iodo-2-(trityloxymethyl)tetrahydrofuran-3-yl benzoate 
• 1147119-15-0 (2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-4,4-difluoro-2-(trityloxymethyl)tetrahydrofuran-3-yl Benzoate 
• 1147119-11-6 (3R,4R)-5-trityloxy-3-benzoyloxy-2,2-difluoro-pentanoic acid γ-lactone 
• 134877-42-2 3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-D-erythro-pentofuranose 
• 1173824-58-2 (2R,3R)-2-((benzoyloxy)methyl)-4,4-difluoro-5-hydroxyoxolan-3-yl benzoate 
• 122111-01-7 2-deoxy-2,2-difluoro-D-erythro-pentonic acid γ-lactone 3,5-dibenzoate 
• 890044-84-5 (2R,3R)-5-acetoxy-2-((benzoyloxy)methyl)-4,4-difluorotetrahydrofuran-3-yl benzoate 
• 946424-25-5 2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-bis(phenylacetate) 

Relevant academic research and scientific papers

Titanium-promoted highly stereoselective synthesis of α,α-difluoro-β,γ-dihydroxyester. Simple route to 2-deoxy-2,2-difluororibose

The highly stereoselective synthesis of α,α-difluoro-β,γ-dihydroxyesters is described.Reformatsky reaction of bromo- or iododifluoroacetate with D-glyceraldehyde provide (3R,4R)-2,2-difluoro-4,5-O-cyclohexylidene-3-triethylsiloxypentanoic acid ethyl ester in high yield, with more than 95percent diastereoselectivity, by asymmetric induction promoted by Cp2TiCl2.The reaction affords a simple and practical route to 2-deoxy-2,2-difluororibose.

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.

Method for synthesizing 2- deoxy -2,2- difluoropentanoic acid -1- ketone -3,5- dibenzoin (by machine translation)

The invention takes 2,2 - dimethyl - 4444444H-1, 3-dioxane - 4 4-one and difluorobromoacetic acid as the reaction raw material, without having a specific chiral configuration, to selectively synthesize a specific configuration cyclization product, under the action of a monovalent copper salt and a chiral ligand . reaction is simpler, and Reformatsky environment-friendly, is avoided under slightly acidic condition by hydrolysis, of, the cyclization product of the cyclization product. The preparation ;NaBH, reduces side reactions. 4 - I2 The reduction system can selectively reduce the carboxylic acid without reducing the reduction effect, of the lactone by . and has the 2 -deoxy - 2222,dibenzofuran sugar - 1 1-ketone - 3333,5-dibenzoin synthesis route, is simple, environment-friendly, total yield . for industrial production, can be effectively reduced. (by machine translation)

Method for preparing Gemcitabine intermediate from chiral catalyst

The invention relates to a method for preparing a Gemcitabine intermediate from a chiral catalyst, and belongs to the technical field of synthesis of medical intermediates. In order to solve the problem that the existing reaction is poor in stereoselectivity, the invention provides the method for preparing the Gemcitabine intermediate from the chiral catalyst; the method comprises the following steps: performing a condensation reaction on R-glyceraldehyde acetonide and difluoro halogenated ethyl acetate in an inert organic solvent under the combined catalytic action of active zinc powder and delta-amino alcohol ligands to obtain a corresponding intermediate; performing deprotection and lactonization treatment on the intermediate and performing a reaction on the intermediate and benzoyl chloride in the presence of an acid-binding agent to obtain the corresponding Gemcitabine intermediate. A product obtained with the method provided by the invention has an ee value being as high as 98% or above, the content of an erythro form product is high, and the obtained product does not need to be refined and can be directly used for next reaction.

Gemcitabine intermediate preparation method

The present invention provides a gemcitabine intermediate preparation method, wherein a compound 1 is adopted as a raw material, and six reactions such as esterification, fluorization, hydrolysis, oxidation, Mitsunobu, and reduction are performed to prepare a compound 7. According to the present invention, the method has characteristics of simple operation and high yield, and is suitable for industrial production. The compounds 1-7 are defined in the specification.

STEREOSELECTIVE SYNTHESIS OF BETA-NUCLEOSIDES

A process of stereoselectively synthesizing β-nucleoside of formula (I), e.g., 2'-deoxy-2,2'-difluorocytidine, is described. The process includes reacting a tetrahydrofuran compound of the following formula: in which wherein R1, R2, R3, R4, and L as defined in the specification, with a nucleobase derivative in the presence of an oxidizing agent.

Novel and Highly Stereoselective Process for Preparing Gemcitabine and Intermediates Thereof

The present invention provides a novel and highly stereoselective process for preparing gemcitabine, which is suitable for industrial production, wherein, it includes the following reactions. Additionally, the invention discloses the key intermediates. The definition for the groups of G1, G2, G3, G4, and G5 are described in the specification.

NOVEL SYNTHESIS OF BETA-NUCLEOSIDES

This invention relates to a process of stereoselectively synthesizing β-nucleoside, e.g., 2′-deoxy-2,2′-difluorocytidine.

A NOVEL AND HIGHLY STEREOSELECTIVE PROCESS FOR PREPARING GEMCITABINE AND INTERMEDIATES THEREOF

The present invention provides a novel and highly stereoselective process for preparing gemcitabine, which is suitable for industrial production, wherein, it includes the following reactions. Additionally, the invention discloses the key intermediates. The definition for the groups of G1, G2, G3, G4, and G5 are described in the specification.

Process for Preparing Gemcitabine and Associated Intermediates

The present invention provides processes for preparing novel chemical substances that are useful as intermediates in the preparation of gemcitabine and processes for preparing gemcitabine therewith. Exemplary intermediates include mixtures of D-erythro and D-threo (3R- and 3S-) isomers of 3-(hydroxy)-2,2-difluoro-3-(2,2-dimethyldioxolan-4-yl)propionic acid salts. Also provided is a novel process for selectively isolating the D-erythro and D-threo isomers of the said salts in purities of at least about 95%, and processes of using them for preparing nucleoside analogs such as, e.g., gemcitabine and intermediates and analogs thereof.