97614-44-3

Basic information

• Product Name: 2-Deoxy-2-fluoro-alpha-D-arabinofuranosyl bromide 3,5-dibenzoate
• Synonyms: 2-Deoxy-2-fluoro-alpha-D-arabinofuranosyl bromide 3,5-dibenzoate;2-Deoxy-2-fluoro-alpha-D-arabinofuranosyl bromide dibenzoate;2-Deoxy-2-Fluoro-a-D-arabinofuranosyl broMide-3,5-dibenzoate;2-Deoxy-2-fluoro-α-D-arabinofuranosyl BroMide 3,5-Dibenzoate;[(2R,3R,4S,5R)-3-(Benzoyloxy)-5-bromo-4-fluorooxolan-2-yl]methyl benzoate
• CAS NO: 97614-44-3
• Molecular Formula: C₁₉H₁₆BrFO₅
• Molecular Weight: 423.2297432
• Mol File: 97614-44-3.mol
• Article Data: 47

Chemical Properties

• Melting Point: 73℃
• Boiling Point: 492.3±45.0 °C(Predicted)
• Appearance: /
• Density: 1.51
• CAS DataBase Reference: 2-Deoxy-2-fluoro-alpha-D-arabinofuranosyl bromide 3,5-dibenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Deoxy-2-fluoro-alpha-D-arabinofuranosyl bromide 3,5-dibenzoate(97614-44-3)
• EPA Substance Registry System: 2-Deoxy-2-fluoro-alpha-D-arabinofuranosyl bromide 3,5-dibenzoate(97614-44-3)

Safety Data

• Hazardous Substances Data: 97614-44-3(Hazardous Substances Data)

Usage

Description

2-Deoxy-2-fluoro-alpha-D-arabinofuranosyl bromide 3,5-dibenzoate is a chemical compound that serves as an intermediate in the synthesis of various pharmaceuticals. It is characterized by the presence of a 2-deoxy-2-fluoro-alpha-D-arabinofuranosyl moiety and a bromide group, along with two benzoate groups at the 3 and 5 positions. This unique structure endows it with properties that make it a valuable component in the development of certain drugs.

Uses

Used in Pharmaceutical Industry:
2-Deoxy-2-fluoro-alpha-D-arabinofuranosyl bromide 3,5-dibenzoate is used as a key intermediate in the synthesis of Clofarabine (C586890), a second-generation purine nucleoside analog. Clofarabine is an antimetabolite that inhibits DNA synthesis and resists deamination by adenosine deaminase, making it an effective antineoplastic agent. Its role in the synthesis of Clofarabine highlights its importance in the development of cancer treatments.
Additionally, 2-Deoxy-2-fluoro-alpha-D-arabinofuranosyl bromide 3,5-dibenzoate is related to the antibiotic Gentamicin, indicating its potential use in the development of new antibiotics or improvements to existing ones. This relationship suggests that the compound may have properties that contribute to the effectiveness of antibiotics, particularly in the context of treating bacterial infections.

Upstream product

• 14215-97-5 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose 
• 491594-58-2 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranose 
• 97614-42-1 2-O-(imidazolylsulfonyl)-1,3,5-tri-O-benzoyl-α-D-ribofuranose 
• 22224-41-5 1,3,5-tri-O-benzoyl-α-D-ribofuranoside 
• 97614-43-2 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose 

Downstream Products

• 1145869-36-8 1-(4'-azido-3'-O-benzoyl-2'-deoxy-2'-fluoro-5'-iodo-β-D-arabinofuranosyl)uracil 
• 1333126-30-9 1-(4-azido-2-deoxy-2-fluoro-3-O-benzoyl-5-O-(3-chlorobenzoyl)-β-D-arabinofuranosyl)uracil 
• 1382358-19-1 1-(2-deoxy-2-fluoro-3,5-di-O-benzoyl-β-D-arabinofuranosyl)-5-iodocytosine 
• 69123-90-6 fiacitabine 
• 123318-82-1 clofarabine 
• 355138-50-0 6-amino-2-chloro-9-(2'-deoxy-2'-fluoro-3',5'-di-O-benzoyl-β-D-arabinofuranosyl)-9H-purine 
• 118373-61-8 2-amino-6-chloro-9-(3',5'-di-O-benzoyl-2'-deoxy-2'-fluoro-β-D-arabinofuranosyl)-9H-purine 

Relevant articles and documents

S-ANTIGEN TRANSPORT INHIBITING OLIGONUCLEOTIDE POLYMERS AND METHODS

Various embodiments provide STOPS? polymers that are S-antigen transport inhibiting oligonucleotide polymers, processes for making them and methods of using them to treat diseases and conditions. In some embodiments the STOPS? modified oligonucleotides include an at least partially phosphorothioated sequence of alternating A and C units having modifications as described herein. The sequence independent antiviral activity against hepatitis B of embodiments of STOPS? modified oligonucleotides, as determined by HBsAg Secretion Assay, is an EC50 that is less than 100 nM.

Synthesis of Rovafovir Etalafenamide (Part IV): Evolution of the Synthetic Process to the Fluorinated Nucleoside Fragment

Fluorinated nucleoside 1 is a key starting material in the synthesis of rovafovir etalafenamide (2), a novel nucleotide reverse transcriptase inhibitor under development at Gilead Sciences for the treatment of HIV. While an initial manufacturing route enabled the production of 1 to support clinical development, alternative approaches were explored to further enhance manufacturing effectiveness, improve processing time, reduce cost, and minimize the environmental impact. Toward this end, two new routes were developed to a key synthetic intermediate, which was converted to 1 using a new protecting group strategy. The new chemistry led to improvements in the manufacturing process while reducing the overall process mass intensity (PMI).

ANTIVIRAL DRUG

PROBLEM TO BE SOLVED: To provide a nucleic acid analog having excellent antiviral activity (particularly anti-hepatitis B virus activity). SOLUTION: The invention provides a compound represented by the formula (I) in the figure, where each symbol is as defined in the specification, or a salt thereof. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT