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(3aR,4S,6R,6aS)-6-Amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol

  • CAS No. 155899-66-4

  • Cat. No. CS-M2377
  • Purity≥98%
  • MDL No.MFCD22690255

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

(3aR,4S,6R,6aS)-6-Amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol|CS-M2377

Structure of 155899-66-4

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General Information

  • CAS No. 155899-66-4
  • Cat. No. CS-M2377
  • Purity ≥98%
  • MDL No. MFCD22690255
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₁₅NO₃
  • Molecular Weight 173.21
  • Synonym(s) None
  • SMILES O[C@H]1C[C@@H](N)[C@H]2[C@@H]1OC(C)(C)O2

Description

This tetrahydrocyclopenta[d][1,3]dioxol derivative features a stereodefined amino-alcohol motif with a rigid, fused bicyclic core. The 6-amino and 4-hydroxyl groups are positioned on adjacent ring systems, enabling directional functionalization. Bench-stable and moisture-tolerant, this scaffold integrates readily into chiral building blocks for medicinal chemistry and natural product synthesis.

Application

(3aR,4S,6R,6aS)-6-Amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol serves as a stereochemically defined, bench-stable building block for the synthesis of complex heterocyclic scaffolds. Its amino and hydroxyl functionalities enable diverse functionalization, including amide coupling and derivatization under mild conditions. The rigid cyclopentadiol core provides structural preorganization, facilitating its use in medicinal chemistry campaigns targeting bioactive molecules with constrained geometries.

Synthesis

  • Route1
    • Ticagrelor Impurity 228|CS-1001682
      155855-51-9
    • ~99%
    • In-stock
      (3aR,4S,6R,6aS)-6-Amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol|CS-M2377
      155899-66-4

    References

    • LEK Pharmaceuticals d.d.; Sterk, Damjan; Casar Zdenko Patent: EP2666771 A1, 2013 ; Location in patent: Paragraph 0074; 0075 ;
  • Route2
    • (3aR,4S,6R,6aS)-6-(Benzylamino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol|CS-0611465
      155855-53-1
    • ~85%
    • In-stock
      (3aR,4S,6R,6aS)-6-Amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol|CS-M2377
      155899-66-4

    References

    • LEK Pharmaceuticals d.d.; Sterk, Damjan; Casar Zdenko Patent: EP2666771 A1, 2013 ; Location in patent: Paragraph 0079; 0080 ;
  • Route3
    • null|null
      155934-55-7
    • ~%
    • In-stock
      (3aR,4S,6R,6aS)-6-Amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol|CS-M2377
      155899-66-4

    References

    • Journal of Organic Chemistry, , vol. 70, # 17 p. 6884 - 6890

Safety Information

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Computational Chemistry Data

  • TPSA   64.71
  • LogP   -0.4016
  • H_Acceptors   4
  • H_Donors   2
  • Rotatable_Bonds   0

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