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CS-W001157 4
Total: USD 88.00

9-[(3aR,4R,6R,6aR)-6-(aminomethyl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]-9H-purin-6-amine

  • CAS No. 21950-36-7

  • Cat. No. CS-D1218
  • Molecule weightNone
  • Purity≥97%
  • MDL No.MFCD15833219

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

9-[(3aR,4R,6R,6aR)-6-(aminomethyl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]-9H-purin-6-amine|CS-D1218

Structure of 21950-36-7

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General Information

  • CAS No. 21950-36-7
  • Cat. No. CS-D1218
  • Purity ≥97%
  • MDL No. MFCD15833219
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₈N₆O₃
  • Molecular Weight None
  • Synonym(s) 5'-Amino-5'-deoxy-2',3'-O-isopropylidineadenosine; 9-[(3aR,4R,6R,6aR)-6-(aminomethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]purin-6-amine
  • SMILES CC1(C)O[C@H]2[C@@H](O1)[C@H](N3C(N=CN=C4N)=C4N=C3)O[C@@H]2CN

Description

This purine derivative features a unique tetrahydrofuro[3,4-d][1,3]dioxole scaffold bearing a strategically positioned aminomethyl group, enabling direct integration into nucleoside analogs. The pendant amine enhances solubility and facilitates conjugation, while the rigid fused ring system ensures conformational stability under standard reaction conditions.

Application

9-[(3aR,4R,6R,6aR)-6-(aminomethyl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]-9H-purin-6-amine serves as a versatile purine scaffold for medicinal chemistry applications. Its functionalized tetrahydrofuro[3,4-d][1,3]dioxole moiety enables site-specific derivatization, while the pendant aminomethyl group facilitates conjugation or salt formation. The molecule exhibits robust bench stability and compatibility with standard peptide coupling and reductive amination protocols, making it suitable for library synthesis and target-oriented drug discovery workflows.

Synthesis

  • Route1
    • null|null
      80860-44-2
    • ~97%
    • In-stock
      9-[(3aR,4R,6R,6aR)-6-(aminomethyl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]-9H-purin-6-amine|CS-D1218
      21950-36-7

    References

    • Reeve, Anne M.; Townsend, Craig A. Tetrahedron, 1998 , vol. 54, # 52 p. 15959 - 15974
  • Route2
    • null|null
      34245-48-2
    • ~92%
    • In-stock
      9-[(3aR,4R,6R,6aR)-6-(aminomethyl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]-9H-purin-6-amine|CS-D1218
      21950-36-7

    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
  • Route3

    References

    • Tetrahedron Letters, , vol. 42, # 18 p. 3153 - 3154

Safety Information

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GHS Pictogram : N/A
GHS No : N/A
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UN#: N/A
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Hazard Statements : N/A
Precautionary Statements : N/A

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Computational Chemistry Data

  • TPSA   123.33
  • LogP   -0.2153
  • H_Acceptors   9
  • H_Donors   2
  • Rotatable_Bonds   2

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