Lot numbers can be found on the outside label of a product:
2-Deoxy-2-fluoro-α-D-arabinofuranose 1,3,5-tribenzoate
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CAS No. 97614-43-2
- Cat. No. CS-W009129
- Purity≥98%
- MDL No.MFCD00083339
*For research and further manufacturing use only, not for direct human use.
Structure of 97614-43-2
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General Information
- CAS No. 97614-43-2
- Cat. No. CS-W009129
- Purity ≥98%
- MDL No. MFCD00083339
- Storage 4°C
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₂₆H₂₁FO₇
- Molecular Weight 464.44
- Synonym(s) 2-Deoxy-2-fluoro-α-D-arabinofuranose 1,3,5-tribenzoate; 2'-Fluoro-2'-deoxy-1,3,5-tri-O-benzoyl-α-D-arabinofuranose; α-D-Arabinofuranose,2-deoxy-2-fluoro-,tribenzoate
- SMILES F[C@@H]1[C@@H](OC(C2=CC=CC=C2)=O)O[C@H](COC(C3=CC=CC=C3)=O)[C@H]1OC(C4=CC=CC=C4)=O
Description
2-Deoxy-2-fluoro-α-D-arabinofuranose 1,3,5-tribenzoate features a fluorinated sugar core with three benzoate esters enabling enhanced stability and solubility in organic media. This protected nucleoside precursor facilitates efficient glycosylation reactions under mild conditions, serving as a key intermediate in the synthesis of fluorinated glycoconjugates and antiviral agents.
Application
2-Deoxy-2-fluoro-α-D-arabinofuranose 1,3,5-tribenzoate serves as a stable, bench-ready glycosyl donor for stereoselective glycosylation reactions. The 2-fluoro group enhances anomeric control through neighboring group participation, while the tribenzoate protection pattern provides excellent stability and orthogonal deprotection compatibility. It facilitates efficient construction of fluorinated nucleoside analogs and complex oligosaccharides under standard glycosylation conditions.
Synthesis
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Route1
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In-stock
22224-41-5 - ~83%
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In-stock
97614-43-2
References
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Nucleosides, nucleotides and nucleic acids, , vol. 22, # 5-8 p. 1343 - 1346
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Route2
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97614-42-1 - ~68%
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In-stock
97614-43-2
References
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EP2177527 A1, ; Page/Page column 11-12 ;
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Route3
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97614-41-0 - ~85%
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In-stock
97614-43-2
References
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Tetrahedron, , vol. 54, # 28 p. 8223 - 8240
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Safety Information
Download SDS|
GHS Pictogram :
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GHS No : GHS07
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Signal Word : Warning
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UN#: N/A
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Class : N/A
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Packing Group : N/A
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Hazard Statements : H302-H315-H319-H335
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Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501
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Quality Control
Computational Chemistry Data
- TPSA 88.13
- LogP 3.989
- H_Acceptors 7
- H_Donors 0
- Rotatable_Bonds 7
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Other Classifications
- Chemical Biology Pharmaceutical Development and Drug Discovery Research Conjugation Chemistry/Click Chemistry Aldehyde Reactive Fluorophores and Labels
- Chemical Biology Pharmaceutical Development and Drug Discovery Research Nucleic Acid Chemistry Riboses, 2'-Deoxyriboses
- Chemical Biology Pharmaceutical Development and Drug Discovery Research Reagents Nucleic Acid Chemistry Riboses, 2'-Deoxyriboses
- Biochemistry Biochemicals and Reagents Nucleosides, Nucleotides, Oligonucleotides Nucleobases and their Analogs
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Key Words
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