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(Tetrahydro-2H-pyran-4-yl)methanol

  • CAS No. 14774-37-9

  • Cat. No. CS-D1227
  • Purity≥98%
  • MDL No.MFCD00457804

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

(Tetrahydro-2H-pyran-4-yl)methanol|CS-D1227

Structure of 14774-37-9

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General Information

  • CAS No. 14774-37-9
  • Cat. No. CS-D1227
  • Purity ≥98%
  • MDL No. MFCD00457804
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₁₂O₂
  • Molecular Weight 116.16
  • Synonym(s) None
  • SMILES OCC1CCOCC1

Description

Tetrahydro-2H-pyran-4-yl)methanol serves as a robust protecting group for alcohols, offering high stability under basic and mildly acidic conditions. This hydroxymethyl derivative integrates seamlessly into complex synthetic sequences, where its orthogonality to other functional groups enables selective deprotection. The tetrahydropyranyl moiety provides excellent solubility in common organic solvents and facilitates purification via standard chromatographic methods.

Application

(Tetrahydro-2H-pyran-4-yl)methanol serves as a versatile protecting group for alcohols and a key building block in carbohydrate chemistry. Its tetrahydropyran ring provides excellent stability under a range of reaction conditions, while the pendant hydroxymethyl group enables selective transformations. The molecule facilitates orthogonal protection strategies and functions effectively in multi-step syntheses requiring robust functional group tolerance and ease of removal under mild acidic conditions.

Synthesis

  • Route1

    References

    • PROSIDION LIMITED Patent: WO2006/16174 A1, 2006 ; Location in patent: Page/Page column 13 ; WO 2006/016174 A1
  • Route2

    References

    • Wessig, Pablo; Muehling, Olaf Helvetica Chimica Acta, 2003 , vol. 86, # 3 p. 865 - 893
  • Route3

    References

    • Justus Liebigs Annalen der Chemie, , vol. 525, p. 292,294

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   29.46
  • LogP   0.4053
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   1

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