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3,6-Dihydro-2H-pyran-4-yl trifluoromethanesulfonate

  • CAS No. 188975-30-6

  • Cat. No. CS-B0642
  • Purity≥95%
  • MDL No.MFCD09997709

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

3,6-Dihydro-2H-pyran-4-yl trifluoromethanesulfonate|CS-B0642

Structure of 188975-30-6

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General Information

  • CAS No. 188975-30-6
  • Cat. No. CS-B0642
  • Purity ≥95%
  • MDL No. MFCD09997709
  • Storage -20°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₇F₃O₄S
  • Molecular Weight 232.18
  • Synonym(s) Trifluoromethanesulfonic acid 3,6-dihydro-2H-pyran-4-yl ester
  • SMILES O=S(C(F)(F)F)(OC1=CCOCC1)=O

Description

This triflate ester enables efficient C–O bond formation in synthetic sequences, featuring a reactive pyran-4-yl scaffold that facilitates selective functionalization. The electron-deficient trifluoromethanesulfonate group promotes rapid displacement under mild conditions, while the dihydropyran framework offers stability and compatibility with diverse reaction environments.

Application

3,6-Dihydro-2H-pyran-4-yl trifluoromethanesulfonate serves as a stable, bench-ready glycosyl donor that facilitates efficient O-glycosylation reactions. Its triflate leaving group enables selective activation under mild conditions, supporting high stereoselectivity in the construction of glycoconjugates and complex oligosaccharides. The molecule exhibits excellent functional group tolerance and simplifies purification due to its crystalline nature and low reactivity toward nucleophiles prior to activation.

Synthesis

  • Route1

    References

    • Jana, Navendu; Nguyen, Quyen; Driver, Tom G. Journal of Organic Chemistry, 2014 , vol. 79, # 6 p. 2781 - 2791
  • Route2

    References

    • BRISTOL-MYERS SQUIBB COMPANY; UNIVERSITE DE MONTREAL; PRIESTLEY, Eldon Scott; POSY, Shoshana L.; TREMBLAY, Francois Tremblay; MARTEL, Alain; MARINIER, Anne Patent: WO2013/163241 A1, 2013 ; Location in patent: Paragraph 00181 ;
  • Route3
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      3,6-Dihydro-2H-pyran-4-yl trifluoromethanesulfonate|CS-B0642
      188975-30-6

    References

    • PFIZER INC.; BENBOW, John William; LOU, Jihong; PFEFFERKORN, Jeffrey Allen; TU, Meihua Mike Patent: WO2010/29461 A1, 2010 ; Location in patent: Page/Page column 40 ; WO 2010/029461 A1

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

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Computational Chemistry Data

  • TPSA   52.6
  • LogP   1.1568
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   2

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