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CS-W001157 4
Total: USD 88.00

6-Chloro-9-ribofuranosyl-9H-purine

  • CAS No. 2004-06-0

  • Cat. No. CS-W009440
  • Purity≥97%
  • MDL No.MFCD26142246

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

6-Chloro-9-ribofuranosyl-9H-purine|CS-W009440

Structure of 2004-06-0

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General Information

  • CAS No. 2004-06-0
  • Cat. No. CS-W009440
  • Purity ≥97%
  • MDL No. MFCD26142246
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₁ClN₄O₄
  • Molecular Weight 286.67
  • Synonym(s) None
  • SMILES ClC1=NC=NC2=C1N=CN2C3[C@H](O)[C@H](O)[C@@H](CO)O3

Description

6-Chloro-9-ribofuranosyl-9H-purine is a nucleoside analog featuring a chlorine atom at the 6-position of the purine ring. This substitution enhances metabolic stability and alters base pairing properties, making it valuable for probing RNA structure-function relationships. The ribofuranose sugar moiety supports incorporation into oligonucleotide chains under standard coupling conditions.

Application

6-Chloro-9-ribofuranosyl-9H-purine serves as a key nucleoside building block for the synthesis of modified purine analogs. Its chloro substituent at the C6 position enables regioselective functionalization in downstream coupling reactions, while the ribofuranosyl moiety provides a biologically relevant sugar scaffold. The compound exhibits good bench stability and facilitates efficient incorporation into oligonucleotide and antiviral research workflows.

Synthesis

  • Route1

    References

    • Mathew, Smitha C.; Ghosh, Nandita; By, Youlet; Berthault, Aurelie; Virolleaud, Marie-Alice; Carrega, Louis; Chouraqui, Gaelle; Commeiras, Laurent; Condo, Jocelyne; Attolini, Mireille; Gaudel-Siri, Anouk; Ruf, Jean; Parrain, Jean-Luc; Rodriguez, Jean; Guieu, Regis Bioorganic and Medicinal Chemistry Letters, 2009 , vol. 19, # 23 p. 6736 - 6739
  • Route2
    • null|null
      3510-73-4
    • ~35%
    • In-stock
      6-Chloro-9-ribofuranosyl-9H-purine|CS-W009440
      2004-06-0

    References

    • Yadav, Vikas; Chu, Chung K.; Rais, Reem H.; Al Safarjalani, Omar N.; Guarcello, Vincenzo; Naguib, Fardos N. M.; El Kouni, Mahmoud H. Journal of Medicinal Chemistry, 2004 , vol. 47, # 8 p. 1987 - 1996
  • Route3

    References

    • Moreau, Christelle; Kirchberger, Tanja; Swarbrick, Joanna M.; Bartlett, Stephen J.; Fliegert, Ralf; Yorgan, Timur; Bauche, Andreas; Harneit, Angelika; Guse, Andreas H.; Potter, Barry V. L. Journal of Medicinal Chemistry, 2013 , vol. 56, # 24 p. 10079 - 10102

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   113.52
  • LogP   -0.9088
  • H_Acceptors   8
  • H_Donors   3
  • Rotatable_Bonds   2

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