1173824-58-2

Basic information

• Product Name: 3,5-Dibenzoyl-DDFR
• Synonyms: 3,5-Dibenzoyl-DDFR
• CAS NO: 1173824-58-2
• Molecular Formula: C₁₉H₁₆F₂O₆
• Molecular Weight: 378.3235464
• Mol File: 1173824-58-2.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 495.925°C at 760 mmHg
• Flash Point: 253.726°C
• Appearance: /
• Density: 1.41
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.579
• Storage Temp.: 2-8°C
• PKA: 9.95±0.70(Predicted)
• CAS DataBase Reference: 3,5-Dibenzoyl-DDFR(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Dibenzoyl-DDFR(1173824-58-2)
• EPA Substance Registry System: 3,5-Dibenzoyl-DDFR(1173824-58-2)

Safety Data

• Hazardous Substances Data: 1173824-58-2(Hazardous Substances Data)

Usage

General Description

3,5-Dibenzoyl-DDFR is a chemical compound that is often used in organic synthesis and pharmaceutical research. It is a derivative of DDFR (2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-phenylbenzylidene)-1-benzofuran-3-carboxylate), which is known for its therapeutic potential. 3,5-Dibenzoyl-DDFR has been studied for its antidiabetic, antioxidant, and anti-inflammatory properties, making it a potential candidate for the development of new drugs for the treatment of various medical conditions. Additionally, it has shown promise in the treatment of neurodegenerative diseases and cancer. This chemical compound has garnered interest in the scientific community for its diverse biological activities and potential applications in medicine.

InChI:InChI=1/C19H16F2O6/c20-19(21)15(27-17(23)13-9-5-2-6-10-13)14(26-18(19)24)11-25-16(22)12-7-3-1-4-8-12/h1-10,14-15,18,24H,11H2/t14-,15-,18?/m1/s1

Upstream product

• 122111-01-7 2-deoxy-2,2-difluoro-D-erythro-pentonic acid γ-lactone 3,5-dibenzoate 
• 98-88-4 benzoyl chloride 
• 95058-77-8 2-deoxy-2,2-difluoro-1-carbonylribose 
• 928797-50-6 ethyl (3R,S)-2,2-difluoro-3-hydroxy-(2,2-dimethyldioxolpent-4-yl)propionate 

Downstream Products

• 134877-42-2 3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-D-erythro-pentofuranose 
• 143157-23-7 1-(2'-deoxy-2',2'-difluoro-3',5'-di-O-benzoyl-D-ribofuranosyl)-4-acetamidopyrimidin-2-one 
• 103882-84-4 2’-deoxy-2’,2’-difluoro-cytidine 
• 134790-40-2 C₂₃H₁₉F₂N₃O₆ 
• 134790-39-9 (2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate 
• 134877-42-2 2-deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-diphenylmethyl ester-1-methanesulfonate 
• 134877-43-3 α-D-erythropentafuranose-2'-deoxy-2',2'-difluoro-3,5-dibenzoate-1-methanesulfonate 
• 908337-63-3 2¹-deoxy-2¹,2¹-difluoro-3,5-bis-O-benzoyl-D-ribose trichloroacetimidate 
• 1151529-00-8 1-O-triisopropylsilyl-2-deoxy-2,2-difluoro-3,5-di-O-benzoyl-D-arabinofuranose 
• 122111-03-9 gemcitabine hydrochloride 
• 1213750-68-5 1,1,3,3-tetramethyl-2-(2'-deoxy-2',2'-difluoro-3',5'-di-O-benzoyl-D-ribofuranosyl)isouronium chloride 
• 1213750-81-2 1,1,3,3-tetramethyl-2-(2'-deoxy-2',2'-difluoro-3',5'-di-O-benzoyl-D-ribofuranosyl)isouronium triflate 
• 1213750-85-6 1,1,3,3-tetramethyl-2-(2'-deoxy-2',2'-difluoro-3',5'-di-benzoyl-D-ribofuranosyl)isouronium triflate α-anomer 
• 95058-80-3 1-(2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)thymine 

Relevant articles and documents

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).

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.