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N4-Benzoyl-2'-fluoro-2'-deoxycytidine

  • CAS No. 146954-76-9

  • Cat. No. CS-0172704
  • Purity≥98%
  • MDL No.MFCD22373353

*For research and further manufacturing use only, not for direct human use.

N4-Benzoyl-2'-fluoro-2'-deoxycytidine|CS-0172704

Structure of 146954-76-9

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General Information

  • CAS No. 146954-76-9
  • Cat. No. CS-0172704
  • Purity ≥98%
  • MDL No. MFCD22373353
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₆H₁₆FN₃O₅
  • Molecular Weight 349.32
  • Synonym(s) None
  • SMILES O[C@H]1[C@@H](F)[C@H](N2C(N=C(NC(C3=CC=CC=C3)=O)C=C2)=O)O[C@@H]1CO

Description

N-Benzoyl-2′-deoxy-2′-fluorocytidine features a fluorinated sugar moiety that enhances nucleic acid stability and resistance to enzymatic degradation. The benzoyl group at the N4 position provides steric protection and improves solubility in organic solvents. This compound serves as a key building block for synthesizing modified oligonucleotides with enhanced bioavailability and nuclease resistance, particularly in antisense and siRNA applications.

Application

N-Benzoyl-2′-deoxy-2′-fluorocytidine serves as a key nucleoside building block for the synthesis of antiviral agents and oligonucleotide therapeutics. The 2′-fluoro substitution enhances metabolic stability and nuclease resistance, while the N-benzoyl group provides orthogonal protection during phosphoramidite coupling. This derivative exhibits excellent bench stability, facilitates efficient solid-phase synthesis, and enables site-specific incorporation into DNA strands with improved duplex affinity.

Safety Information

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GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362-P405-P501

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Computational Chemistry Data

  • TPSA   113.68
  • LogP   0.0843
  • H_Acceptors   7
  • H_Donors   3
  • Rotatable_Bonds   4

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