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CS-W001157 4
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5'-O-DMT-2'-TBDMS-Uridine

  • CAS No. 81246-80-2

  • Cat. No. CS-0154964
  • Molecule weight660.83
  • Purity≥98%
  • MDL No.MFCD00135726

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

5'-O-DMT-2'-TBDMS-Uridine|CS-0154964

Structure of 81246-80-2

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General Information

  • CAS No. 81246-80-2
  • Cat. No. CS-0154964
  • Purity ≥98%
  • MDL No. MFCD00135726
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₃₆H₄₄N₂O₈Si
  • Molecular Weight 660.83
  • Synonym(s) None
  • SMILES O[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](N2C(NC(C=C2)=O)=O)O[C@@H]1COC(C3=CC=C(OC)C=C3)(C4=CC=C(OC)C=C4)C5=CC=CC=C5

Description

5'-O-DMT-2'-TBDMS-Uridine features a dimethoxytrityl group at the 5'-position and a tert-butyldimethylsilyl group at the 2'-position, providing robust protection for synthetic oligonucleotide assembly. This dual protection enhances stability during phosphoramidite coupling cycles and simplifies purification. The molecule combines excellent solubility with bench-stable handling, enabling efficient incorporation into RNA sequences under standard synthesis conditions.

Application

5'-O-DMT-2'-TBDMS-Uridine serves as a key building block for the synthesis of oligonucleotides requiring site-specific protection and controlled reactivity. The DMT group at the 5'-position enables efficient purification via reverse-phase chromatography, while the TBDMS protection at the 2'-OH ensures stability during synthetic cycles and prevents undesired side reactions. This derivative facilitates reliable coupling in automated solid-phase synthesis and is widely used in the construction of modified RNA strands with enhanced nuclease resistance and defined structural integrity.

Synthesis

  • Route1
    • null|null
      18162-48-6
    • In-stock
      5'-O-DMT-rU|CS-0159302
      81246-79-9
    • ~91%
    • In-stock
      5'-O-DMT-2'-TBDMS-Uridine|CS-0154964
      81246-80-2

    References

    • Sun, Xixi; Lee, Hyelee; Lee, Sunggi; Tan, Kian L. Nature Chemistry, 2013 , vol. 5, # 9 p. 790 - 795
  • Route2
    • null|null
      18162-48-6
    • In-stock
      5'-O-DMT-rU|CS-0159302
      81246-79-9
    • ~4%
    • 1-((2R,3R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-((tert-butyldimethylsilyl)oxy)-3-hydroxytetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione|CS-0571553
      81246-81-3
    • In-stock
      5'-O-DMT-2'-TBDMS-Uridine|CS-0154964
      81246-80-2

    References

    • Hakimelahi, Gholam H.; Proba, Zbigniew A.; Ogilvie, Kelvin K. Tetrahedron Letters, 1981 , vol. 22, # 52 p. 5243 - 5246
  • Route3

    References

    • Serebryany; Beigelman Nucleosides, nucleotides and nucleic acids, 2003 , vol. 22, # 5-8 p. 1007 - 1009

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   121.24
  • LogP   5.2112
  • H_Acceptors   9
  • H_Donors   2
  • Rotatable_Bonds   11

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