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((3aR,6S,6aR)-6-(Benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5,5-diyl)dimethanol

  • CAS No. 63593-03-3

  • Cat. No. CS-0053055
  • Purity≥97%
  • MDL No.None

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

((3aR,6S,6aR)-6-(Benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5,5-diyl)dimethanol|CS-0053055

Structure of 63593-03-3

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General Information

  • CAS No. 63593-03-3
  • Cat. No. CS-0053055
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₆H₂₂O₆
  • Molecular Weight 310.34
  • Synonym(s) Furo[2,3-d]-1,3-dioxole,a-D-erythro-pentofuranose deriv
  • SMILES [H][C@@]12OC(C)(C)O[C@]1([H])[C@H](OCC1=CC=CC=C1)C(CO)(CO)O2

Description

This tetrahydrofurodioxole diol features a rigid, oxygen-rich scaffold with benzyloxy and dimethyl substituents that enhance solubility and stability. The geminal diol functionality enables direct use in coupling reactions or derivatization without protection. Designed for efficient integration into complex molecular architectures, it serves as a versatile synthon in medicinal chemistry and natural product synthesis.

Application

(3aR,6S,6aR)-6-(Benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5,5-diyl)dimethanol serves as a stable, bench-ready building block for the synthesis of complex carbohydrate mimetics and heterocyclic scaffolds. Its rigid fused bicyclic core with orthogonal hydroxyl and benzyl ether functionalities enables selective derivatization, facilitating glycosylation studies and targeted functional group interconversions in medicinal chemistry workflows.

Synthesis

  • Route1
    • null|null
      50-00-0
    • null|null
      63593-02-2
    • ~92%
    • In-stock
      ((3aR,6S,6aR)-6-(Benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5,5-diyl)dimethanol|CS-0053055
      63593-03-3

    References

    • Nacro, Kassoum; Lee, Jeewoo; Barchi Jr., Joseph J; Lewin, Nancy E; Blumberg, Peter M; Marquez, Victor E Tetrahedron, 2002 , vol. 58, # 26 p. 5335 - 5345
  • Route2
    • 5-(2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethylfuro[2,3-d][1,3]dioxol-6-ol|CS-0766165
      620630-82-2
    • ~%
    • In-stock
      ((3aR,6S,6aR)-6-(Benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5,5-diyl)dimethanol|CS-0053055
      63593-03-3

    References

    • Swayze, Eric E.; Seth, Punit P. Patent: US2007/249049 A1, 2007 ; Location in patent: Page/Page column 14-15 ;
  • Route3
    • 3-O-Benzyl-1,2:5,6-di-O-isopropylidene-a-D-allofuranose|CS-0468332
      22331-21-1
    • ~%
    • In-stock
      ((3aR,6S,6aR)-6-(Benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5,5-diyl)dimethanol|CS-0053055
      63593-03-3

    References

    • Nacro, Kassoum; Lee, Jeewoo; Barchi Jr., Joseph J; Lewin, Nancy E; Blumberg, Peter M; Marquez, Victor E Tetrahedron, 2002 , vol. 58, # 26 p. 5335 - 5345

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   77.38
  • LogP   0.803
  • H_Acceptors   6
  • H_Donors   2
  • Rotatable_Bonds   5

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