143157-27-1

Basic information

• Product Name: 2',2'-Difluoro-2'-deoxyuridine 3',5'-Dibenzoate
• Synonyms: 2',2'-Difluoro-2'-deoxyuridine 3',5'-Dibenzoate;3,5-Dibenzoate-2,2-difluorouridine;2'-Deoxy-2',2'-difluorouridine 3',5'-dibenzoate;((2R,3R,5R)-3-(benzoyloxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4,4-difluorotetrahydrofuran-2-yl)methyl benzoate
• CAS NO: 143157-27-1
• Molecular Formula: C₂₃H₁₈F₂N₂O₇
• Molecular Weight: 472
• Product Categories: Bases & Related Reagents;Carbohydrates & Derivatives;Heterocycles;Metabolites & Impurities;Nucleotides
• Mol File: 143157-27-1.mol
• Article Data: 12

Chemical Properties

• Appearance: /
• Density: 1.49±0.1 g/cm3(Predicted)
• Solubility: Dichloromethane, Methanol
• PKA: 9.39±0.10(Predicted)
• CAS DataBase Reference: 2',2'-Difluoro-2'-deoxyuridine 3',5'-Dibenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: 2',2'-Difluoro-2'-deoxyuridine 3',5'-Dibenzoate(143157-27-1)
• EPA Substance Registry System: 2',2'-Difluoro-2'-deoxyuridine 3',5'-Dibenzoate(143157-27-1)

Safety Data

• Hazardous Substances Data: 143157-27-1(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Protected 2’,2’-Difluoro-2’-deoxyuridine, a Gemcitabine metabolite.

Upstream product

• 908337-63-3 2¹-deoxy-2¹,2¹-difluoro-3,5-bis-O-benzoyl-D-ribose trichloroacetimidate 
• 66-22-8 uracil 
• 95058-81-4 gemcitabine 
• 98-88-4 benzoyl chloride 
• 114248-23-6 Deoxydifluorouridine 
• 1445381-44-1 (2R,3R,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4,4-difluorotetrahydrofuran-3-yl benzoate 
• 122111-03-9 gemcitabine hydrochloride 
• 134877-42-2 3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-D-erythro-pentofuranose 
• 10457-14-4 O,O'-bis-(trimethylsilyl)uracil 
• 890044-84-5 (2R,3R)-5-acetoxy-2-((benzoyloxy)methyl)-4,4-difluorotetrahydrofuran-3-yl benzoate 
• 134877-42-2 2-deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-diphenylmethyl ester-1-methanesulfonate 

Downstream Products

• 114248-23-6 Deoxydifluorouridine 
• 1445381-68-9 C₃₁H₃₁F₂N₃O₅ 

Relevant articles and documents

Influence of 4′-Substitution on the Activity of Gemcitabine and Its ProTide against VZV and SARS-CoV-2

In addition to its therapeutic value as a chemotherapy drug, gemcitabine is of ongoing interest to the scientific community for its broad-spectrum antiviral activity. Herein the synthesis of 4′-methoxy- and 4′-fluoro-substituted gemcitabine analogues along with their phosphoramidate prodrugs is described. Among these derivatives, 4′-fluorogemcitabine proved to be active against varicella zoster virus (VZV, TK+ strain) with an EC50 of 0.042 μM and produced significant cytotoxicity (CC50 = 0.11 μM). Upon derivatization of this trifluoro nucleoside as its prodrug, decreased anti-VZV activity was observed, but with a concomitantly improved selectivity index (SI = 36). When this prodrug was tested against severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2), its antiviral activity (EC50 = 0.73 μM) was comparable to or slightly lower than its cytotoxic concentration in measurements of cell growth and cell morphology, respectively.

A linear synthesis of gemcitabine

Gemcitabine, 2′-deoxy-2′,2′-difluorocytidine, is currently prescribed against a number of cancers. Here we report a linear synthesis of gemcitabine with a high-yielding direct conversion of 3,5-di-O-benzoyl-2-deoxy-2,2-difluororibose into the corresponding glycosyl urea as the key step, followed by conventional conversion to the cytosine base via the uracil derivative. The process proceeded with modest anomeric selectivity.

SUBSTITUTED NUCLEOSIDES, NUCLEOTIDES AND ANALOGS THEREOF

Disclosed herein are nucleosides, nucleotides and nucleotide analogs, methods of synthesizing the same and methods of treating diseases and/or conditions such as a Picornavirus and/or Flaviviridae infection with one or more nucleosides, nucleotides and nucleotide analogs.