95058-77-8

Basic information

• Product Name: 2-Deoxy-2,2-difluoro -D-threo-pentonic acid γ-lactone
• Synonyms: 2-Deoxy-2,2-difluoro -D-threo-pentonic acid γ-lactone;2-deoxy-2,2-difluoro-D-erythro-Pentonic acid gamma-Lactone
• CAS NO: 95058-77-8
• Molecular Formula: C₅H₆F₂O₄
• Molecular Weight: 168.0955464
• Mol File: 95058-77-8.mol
• Article Data: 17

Chemical Properties

• Melting Point: 271-273 °C (decomp)
• Boiling Point: 348.5±42.0 °C(Predicted)
• Appearance: /
• Density: 1.62±0.1 g/cm3(Predicted)
• PKA: 10.24±0.60(Predicted)
• CAS DataBase Reference: 2-Deoxy-2,2-difluoro -D-threo-pentonic acid γ-lactone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Deoxy-2,2-difluoro -D-threo-pentonic acid γ-lactone(95058-77-8)
• EPA Substance Registry System: 2-Deoxy-2,2-difluoro -D-threo-pentonic acid γ-lactone(95058-77-8)

Safety Data

• Hazardous Substances Data: 95058-77-8(Hazardous Substances Data)

Usage

General Description

2-Deoxy-2,2-difluoro-D-threo-pentonic acid γ-lactone, also known as 2,2-difluoroglyuronic acid γ-lactone, is a synthetic chemical compound with a lactone structure. It is a derivative of the sugar D-threose, with fluorine atoms replacing two of the hydroxyl groups. 2-Deoxy-2,2-difluoro -D-threo-pentonic acid γ-lactone is known for its potent inhibitory effects on enzymes involved in carbohydrate metabolism, making it a potential drug candidate for the treatment of diabetes and other metabolic disorders. Its unique structure and properties have also made it a subject of interest in medicinal and synthetic organic chemistry research.

Upstream product

• 667-27-6 Ethyl bromodifluoroacetate 
• 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 
• 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 
• 909411-33-2 C₂₁H₁₈F₂O₆ 
• 946424-26-6 2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-diacetate 
• 628-13-7 pyridine hydrochloride 
• 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 
• 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) 
• 122111-01-7 2-deoxy-2,2-difluoro-D-erythro-pentonic acid γ-lactone 3,5-dibenzoate 
• 122111-02-8 2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate 

Relevant articles and documents

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.

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)

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.