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CS-W001157 4
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(1S,2R)-1-((2R,3R,4S)-3-Acetamido-4-azido-6-(methoxycarbonyl)-3,4-dihydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate

  • CAS No. 130525-58-5

  • Cat. No. CS-0081277
  • Purity≥98%
  • MDL No.MFCD08704809

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

(1S,2R)-1-((2R,3R,4S)-3-Acetamido-4-azido-6-(methoxycarbonyl)-3,4-dihydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate|CS-0081277

Structure of 130525-58-5

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General Information

  • CAS No. 130525-58-5
  • Cat. No. CS-0081277
  • Purity ≥98%
  • MDL No. MFCD08704809
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₈H₂₄N₄O₁₀
  • Molecular Weight 456.40
  • Synonym(s) Zanamivir Azide Triacetate Methyl Ester
  • SMILES CC(OC[C@@H](OC(C)=O)[C@H]([C@@]1([H])[C@@H]([C@H](C=C(C(OC)=O)O1)N=[N+]=[N-])NC(C)=O)OC(C)=O)=O

Description

This triacetate derivative features a chiral glycosyl scaffold with orthogonal functional handles: an azide group for bioorthogonal conjugation and a masked hydroxyl array for controlled deprotection. The (1S,2R)-configured propanediol backbone ensures stereoselective reactivity in glycoconjugate synthesis, while the acetate esters provide enhanced solubility and stability under standard bench conditions.

Synthesis

  • Route1
    • null|null
      78850-37-0
    • ~96%
    • In-stock
      (1S,2R)-1-((2R,3R,4S)-3-Acetamido-4-azido-6-(methoxycarbonyl)-3,4-dihydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate|CS-0081277
      130525-58-5

    References

    • CATABASIS PHARMACEUTICALS, INC.; MILNE, Jill C.; JIROUSEK, Michael R.; VU, Chi B.; WENSLEY, Allison; TING, Amal Patent: WO2013/90420 A2, 2013 ; Location in patent: Paragraph 00176 ;
  • Route2
    • null|null
      366018-39-5
    • ~73%
    • In-stock
      (1S,2R)-1-((2R,3R,4S)-3-Acetamido-4-azido-6-(methoxycarbonyl)-3,4-dihydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate|CS-0081277
      130525-58-5

    References

    • TSRL, INC.; HILFINGER, John; SHEN, Wei Patent: WO2011/123856 A1, 2011 ; Location in patent: Page/Page column 42 ; WO 2011/123856 A1
  • Route3
    • null|null
      163860-77-3
    • ~98%
    • In-stock
      (1S,2R)-1-((2R,3R,4S)-3-Acetamido-4-azido-6-(methoxycarbonyl)-3,4-dihydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate|CS-0081277
      130525-58-5

    References

    • Liu, Ke-Gang; Yan, Shi; Wu, Yu-Lin; Yao, Zhu-Jun Organic Letters, 2004 , vol. 6, # 13 p. 2269 - 2272

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-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   192.29
  • LogP   0.0522
  • H_Acceptors   11
  • H_Donors   1
  • Rotatable_Bonds   9

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