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CS-W001157 4
Total: USD 88.00

5'-Chloro-5'-deoxyadenosine

  • CAS No. 892-48-8

  • Cat. No. CS-W000275
  • Purity≥96%
  • MDL No.MFCD00049038

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

5'-Chloro-5'-deoxyadenosine|CS-W000275

Structure of 892-48-8

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General Information

  • CAS No. 892-48-8
  • Cat. No. CS-W000275
  • Purity ≥96%
  • MDL No. MFCD00049038
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₂ClN₅O₃
  • Molecular Weight 285.69
  • Synonym(s) adenosine, 5'-chloro-5'-deoxy-
  • SMILES O[C@@H]1[C@H](O)[C@@H](CCl)O[C@H]1N2C=NC3=C2N=CN=C3N

Description

5'-Chloro-5'-deoxyadenosine features a chlorine atom at the 5' position of the ribose moiety, conferring enhanced metabolic stability and resistance to enzymatic degradation. This modification enables prolonged intracellular retention and facilitates targeted incorporation into nucleic acid strands during synthetic oligonucleotide assembly. The chloro-substituted analog serves as a key building block in the development of site-specifically modified nucleoside probes for biochemical and therapeutic applications.

Application

5'-Chloro-5'-deoxyadenosine serves as a valuable nucleoside building block for the synthesis of modified oligonucleotides and antiviral agents. Its 5'-chloro substituent enables efficient coupling in solid-phase synthesis and facilitates downstream functionalization via nucleophilic displacement. The molecule exhibits good bench stability and compatibility with standard protecting group strategies, making it a practical choice for medicinal chemistry campaigns targeting nucleoside analogs.

Synthesis

  • Route1
    • Adenosine Bucladesine  Impurity|CS-0228878
      58-61-7
    • ~92%
    • In-stock
      5'-Chloro-5'-deoxyadenosine|CS-W000275
      892-48-8

    References

    • Journal of Medicinal Chemistry, , vol. 55, # 18 p. 8066 - 8074,9
  • Route2
    • null|null
      662131-88-6
    • ~95%
    • In-stock
      5'-Chloro-5'-deoxyadenosine|CS-W000275
      892-48-8

    References

    • European Journal of Organic Chemistry, , # 24 p. 4748 - 4751
  • Route3
    • null|null
      69260-62-4
    • ~94%
    • In-stock
      5'-Chloro-5'-deoxyadenosine|CS-W000275
      892-48-8

    References

    • Canadian Journal of Chemistry, , vol. 69, # 9 p. 1468 - 1474

Safety Information

Download SDS
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-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   119.31
  • LogP   -0.7335
  • H_Acceptors   8
  • H_Donors   3
  • Rotatable_Bonds   2

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