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Tri-O-Acetyl-D-galactal

  • CAS No. 4098-06-0

  • Cat. No. CS-0098176
  • Purity≥95%
  • MDL No.MFCD00064092

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

Tri-O-Acetyl-D-galactal|CS-0098176

Structure of 4098-06-0

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General Information

  • CAS No. 4098-06-0
  • Cat. No. CS-0098176
  • Purity ≥95%
  • MDL No. MFCD00064092
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₆O₇
  • Molecular Weight None
  • Synonym(s) None
  • SMILES O=C(O[C@H]1[C@@H](OC(C)=O)[C@@H](COC(C)=O)OC=C1)C

Description

Tri-O-Acetyl-D-galactal features a protected galactal scaffold with three acetyl groups, offering enhanced stability and solubility in organic solvents. This derivative serves as a key glycosyl donor in automated oligosaccharide synthesis, enabling efficient glycosidation reactions under mild conditions.

Application

Tri-O-Acetyl-D-galactal serves as a stable, bench-ready glycal building block for carbohydrate synthesis, enabling efficient glycosylation reactions via its reactive anomeric center. The acetyl groups provide enhanced solubility and stability while allowing orthogonal deprotection strategies. It functions as a key intermediate in the construction of complex oligosaccharides and glycoconjugates, particularly in the synthesis of bioactive glycans and glycosidase inhibitors.

Synthesis

  • Route1

    References

    • Kovacs, Gyoengyver; Gyarmati, Julianna; Somsak, Laszlo; Micskei, Karoly Tetrahedron Letters, 1996 , vol. 37, # 8 p. 1293 - 1296
  • Route2

    References

    • Pilgrim, Wayne; Murphy, Paul V. Organic Letters, 2009 , vol. 11, # 4 p. 939 - 942
  • Route3
    • In-stock
      Acetobromo-α-D-galactose|CS-0072837
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      Tri-O-Acetyl-D-galactal|CS-0098176
      4098-06-0
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      13121-62-5

    References

    • Fuerstner, Alois; Baumgartner, Judith; Jumbam, Denis N. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993 , # 1 p. 131 - 138

Safety Information

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GHS Pictogram : N/A
GHS No : N/A
Signal Word : N/A
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : N/A
Precautionary Statements : N/A

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Computational Chemistry Data

  • TPSA   88.13
  • LogP   0.3254
  • H_Acceptors   7
  • H_Donors   0
  • Rotatable_Bonds   4

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