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CS-W001157 4
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Methyl tetra-O-acetyl-β-D-glucopyranuronate

  • CAS No. 7355-18-2

  • Cat. No. CS-W008523
  • Purity≥95%
  • MDL No.MFCD00069834

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

Methyl tetra-O-acetyl-β-D-glucopyranuronate|CS-W008523

Structure of 7355-18-2

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General Information

  • CAS No. 7355-18-2
  • Cat. No. CS-W008523
  • Purity ≥95%
  • MDL No. MFCD00069834
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₅H₂₀O₁₁
  • Molecular Weight 376.31
  • Synonym(s) None
  • SMILES CC(O[C@H]1[C@@H]([C@H](O[C@H]([C@@H]1OC(C)=O)OC(C)=O)C(OC)=O)OC(C)=O)=O

Description

Methyl tetra-O-acetyl-β-D-glucopyranuronate features a fully acetylated pyranose ring with β-configuration, offering enhanced stability and solubility in organic solvents. This derivative serves as a protected building block for glycosylation reactions and structural studies of uronic acid-containing polysaccharides.

Application

Methyl tetra-O-acetyl-β-D-glucopyranuronate serves as a key building block in the synthesis of glycosaminoglycans and related carbohydrate-based scaffolds. Its acetylated hydroxyl groups enhance stability and facilitate selective deprotection, enabling controlled glycosylation reactions. The β-configured glucopyranuronate moiety supports reliable stereochemical control in oligosaccharide assembly, making it valuable for synthetic studies requiring precise structural fidelity.

Synthesis

  • Route1
    • null|null
      67-56-1
    • (3S,3aR,6R,6aR)-3,5,6-Trihydroxytetrahydrofuro[3,2-b]furan-2(3H)-one|CS-0536090
      63-29-6
    • null|null
      108-24-7
    • ~63%
    • In-stock
      Methyl tetra-O-acetyl-β-D-glucopyranuronate|CS-W008523
      7355-18-2

    References

    • TIBOTEC BVBA Patent: WO2004/58787 A2, 2004 ; Location in patent: Page 29-30 ;
  • Route2
    • null|null
      67-56-1
    • (3S,3aR,6R,6aR)-3,5,6-Trihydroxytetrahydrofuro[3,2-b]furan-2(3H)-one|CS-0536090
      63-29-6
    • null|null
      124-41-4
    • null|null
      108-24-7
    • ~46%
    • In-stock
      Methyl tetra-O-acetyl-β-D-glucopyranuronate|CS-W008523
      7355-18-2

    References

    • ACADEMIA SINICA; PRIJOVIC, Zeljko, M.; LEU, Yu-Lin; ROFFLER, Steve, R. Patent: WO2011/66418 A1, 2011 ; Location in patent: Page/Page column 23 ; WO 2011/066418 A1
  • Route3
    • Methyl (2S,3S,4S,5R)-3,4,5,6-tetrahydroxytetrahydro-2H-pyran-2-carboxylate|CS-0569694
      82228-14-6
    • null|null
      75-36-5
    • ~89%
    • In-stock
      Methyl tetra-O-acetyl-β-D-glucopyranuronate|CS-W008523
      7355-18-2

    References

    • Tiwari, Pallavi; Misra, Anup Kumar Carbohydrate Research, 2006 , vol. 341, # 3 p. 339 - 350

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   140.73
  • LogP   -0.7575
  • H_Acceptors   11
  • H_Donors   0
  • Rotatable_Bonds   5

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