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CS-W001157 4
Total: USD 88.00

6-Chloro-9-[2,3-O-(1-methylethylidene)-beta-D-ribofuranosyl]-9H-Purine

  • CAS No. 39824-26-5

  • Cat. No. CS-W000282
  • Molecule weight326.74
  • Purity≥97%
  • MDL No.MFCD03788833

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

6-Chloro-9-[2,3-O-(1-methylethylidene)-beta-D-ribofuranosyl]-9H-Purine|CS-W000282

Structure of 39824-26-5

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General Information

  • CAS No. 39824-26-5
  • Cat. No. CS-W000282
  • Purity ≥97%
  • MDL No. MFCD03788833
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₅ClN₄O₄
  • Molecular Weight 326.74
  • Synonym(s) 6-Chloropurine-9-(2,3-isopropylidene-β-D-ribofuranoside)
  • SMILES CC1(C)O[C@H]2[C@@H](O1)[C@H](N3C(N=CN=C4Cl)=C4N=C3)O[C@@H]2CO

Description

6-Chloro-9-[2,3-O-(1-methylethylidene)-beta-D-ribofuranosyl]-9H-Purine features a protected ribose moiety that enhances stability and facilitates controlled incorporation into nucleic acid analogs. The chlorinated purine base supports efficient coupling in oligonucleotide synthesis workflows, offering improved resistance to hydrolysis under standard conditions.

Application

6-Chloro-9-[2,3-O-(1-methylethylidene)-β-D-ribofuranosyl]-9H-purine serves as a key nucleoside building block for the synthesis of antiviral agents and purine-based pharmaceutical intermediates. The protected ribose moiety enhances stability and facilitates selective functionalization at the C-6 position. Its well-documented reactivity enables reliable glycosylation and coupling protocols in medicinal chemistry workflows, supporting scalable synthesis of nucleoside analogs with proven biological activity.

Synthesis

  • Route1
    • In-stock
      6-Chloro-9-ribofuranosyl-9H-purine|CS-W009440
      2004-06-0
    • null|null
      67-64-1
    • ~95%
    • In-stock
      6-Chloro-9-[2,3-O-(1-methylethylidene)-beta-D-ribofuranosyl]-9H-Purine|CS-W000282
      39824-26-5

    References

    • Zhu, Zhengxiang; Buolamwini, John K. Bioorganic and Medicinal Chemistry, 2008 , vol. 16, # 7 p. 3848 - 3865
  • Route2
    • In-stock
      6-Chloro-9-ribofuranosyl-9H-purine|CS-W009440
      2004-06-0
    • null|null
      77-76-9
    • ~99%
    • In-stock
      6-Chloro-9-[2,3-O-(1-methylethylidene)-beta-D-ribofuranosyl]-9H-Purine|CS-W000282
      39824-26-5

    References

    • MILLENNIUM PHARMACEUTICALS, INC. Patent: WO2006/84281 A1, 2006 ; Location in patent: Page/Page column 78-79 ;
  • Route3
    • (2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(6-oxo-1H-purin-9(6H)-yl)tetrahydrofuran-3,4-diyl diacetate Cytarabine Impurity|CS-0168210
      3181-38-2
    • ~%
    • In-stock
      6-Chloro-9-[2,3-O-(1-methylethylidene)-beta-D-ribofuranosyl]-9H-Purine|CS-W000282
      39824-26-5

    References

    • Camp, David; Li, Ying; McCluskey, Adam; Moni, Roger W.; Quinn, Ronald J. Bioorganic and Medicinal Chemistry Letters, 1998 , vol. 8, # 6 p. 695 - 698

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

Quality Control

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Computational Chemistry Data

  • TPSA   91.52
  • LogP   0.8895
  • H_Acceptors   8
  • H_Donors   1
  • Rotatable_Bonds   2

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