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CS-W001157 4
Total: USD 88.00

1-((2R,4S,5R)-4-((tert-Butyldimethylsilyl)oxy)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione

  • CAS No. 40733-27-5

  • Cat. No. CS-0161988
  • Purity≥97%
  • MDL No.MFCD01631040

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

1-((2R,4S,5R)-4-((tert-Butyldimethylsilyl)oxy)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione|CS-0161988

Structure of 40733-27-5

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General Information

  • CAS No. 40733-27-5
  • Cat. No. CS-0161988
  • Purity ≥97%
  • MDL No. MFCD01631040
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₆H₂₈N₂O₅Si
  • Molecular Weight 356.49
  • Synonym(s) None
  • SMILES OC[C@@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](N2C(NC(C(C)=C2)=O)=O)O1

Description

3’-O-t-Butyldimethylsilylthymidine features a protected 3’-hydroxyl group, enabling stable storage and selective coupling in oligonucleotide synthesis. The silyl moiety provides robust resistance to hydrolysis under standard conditions while allowing facile deprotection with fluoride sources. This derivative facilitates efficient chain elongation in nucleoside-based workflows.

Application

3’-O-Tert-butyldimethylsilylthymidine serves as a protected thymidine building block for nucleoside synthesis, offering enhanced stability and ease of purification. The silyl group enables selective 3’-functionalization while tolerating standard coupling conditions, facilitating efficient oligonucleotide assembly and protecting against degradation during storage and handling.

Synthesis

  • Route1
    • null|null
      40733-26-4
    • ~87%
    • In-stock
      1-((2R,4S,5R)-4-((tert-Butyldimethylsilyl)oxy)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione|CS-0161988
      40733-27-5

    References

    • Tronchet, Jean M. J.; Kovacs, Imre; Dilda, Pierre; Seman, Michel; Andrei, Graciela; Snoeck, Robert; De Clercq, Erik; Balzarini, Jan Nucleosides, Nucleotides and Nucleic Acids, 2001 , vol. 20, # 12 p. 1927 - 1939
  • Route2
    • null|null
      80971-33-1
    • ~94%
    • In-stock
      1-((2R,4S,5R)-4-((tert-Butyldimethylsilyl)oxy)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione|CS-0161988
      40733-27-5

    References

    • Patil; Mane; Salunkhe Synthetic Communications, 1994 , vol. 24, # 17 p. 2423 - 2428
  • Route3
    • null|null
      213552-25-1
    • ~10%
    • In-stock
      1-((2R,4S,5R)-4-((tert-Butyldimethylsilyl)oxy)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione|CS-0161988
      40733-27-5

    References

    • Magdalena, Julia; Fernandez, Susana; Ferrero, Miguel; Gotor, Vicente Tetrahedron Letters, 1999 , vol. 40, # 9 p. 1787 - 1790

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   93.55
  • LogP   1.51522
  • H_Acceptors   6
  • H_Donors   2
  • Rotatable_Bonds   4

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