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CS-W001157 4
Total: USD 88.00

cis-2,5-Bis(hydroxymethyl)tetrahydrofuran

  • CAS No. 2144-40-3

  • Cat. No. CS-0005835
  • Purity≥90%
  • MDL No.MFCD07369849

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

cis-2,5-Bis(hydroxymethyl)tetrahydrofuran|CS-0005835

Structure of 2144-40-3

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General Information

  • CAS No. 2144-40-3
  • Cat. No. CS-0005835
  • Purity ≥90%
  • MDL No. MFCD07369849
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₁₂O₃
  • Molecular Weight 132.16
  • Synonym(s) None
  • SMILES OC[C@H]1O[C@@H](CO)CC1

Description

cis-2,5-Bis(hydroxymethyl)tetrahydrofuran features a rigid, electron-rich tetrahydrofuran core with two hydroxymethyl groups in a cis configuration, enabling predictable stereochemical control. This bench-stable scaffold integrates readily into complex molecular architectures, offering high solubility in polar solvents and compatibility with standard synthetic workflows.

Application

cis-2,5-Bis(hydroxymethyl)tetrahydrofuran serves as a versatile chiral building block for the synthesis of nucleoside analogs and glycosylation intermediates. Its rigid tetrahydrofuran core provides defined stereochemistry, while the two primary hydroxyl groups enable selective derivatization via esterification, etherification, or coupling reactions. The compound exhibits excellent bench stability and facilitates efficient protection-deprotection sequences in complex carbohydrate and heterocyclic syntheses.

Synthesis

  • Route1
    • null|null
      592-42-7
    • ~90%
    • In-stock
      cis-2,5-Bis(hydroxymethyl)tetrahydrofuran|CS-0005835
      2144-40-3

    References

    • Roth, Stefanie; Goehler, Sabrina; Cheng, Huan; Stark, Christian B. W. European Journal of Organic Chemistry, 2005 , # 19 p. 4109 - 4118
  • Route2

    References

    • Naemura; Fukuda; Takahashi; Konishi; Hirose; Tobe Tetrahedron Asymmetry, 1993 , vol. 4, # 5 p. 911 - 918
  • Route3
    • 5-Hydroxymethylfurfural, ≥99%|CS-1268396
      67-47-0
    • ~%
    • In-stock
      cis-2,5-Bis(hydroxymethyl)tetrahydrofuran|CS-0005835
      2144-40-3

    References

    • Journal of the American Chemical Society, , vol. 77, p. 393,395 Journal of the Chemical Society, , p. 1,3

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   49.69
  • LogP   -0.4814
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   2

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