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2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl chloride

  • CAS No. 41355-44-6

  • Cat. No. CS-0098189
  • Purity≥97%
  • MDL No.MFCD00047513

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

2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl chloride|CS-0098189

Structure of 41355-44-6

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General Information

  • CAS No. 41355-44-6
  • Cat. No. CS-0098189
  • Purity ≥97%
  • MDL No. MFCD00047513
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₂₀ClNO₈
  • Molecular Weight 365.76
  • Synonym(s) None
  • SMILES CC(O[C@H]1[C@H]([C@H](O[C@@H]([C@@H]1NC(C)=O)Cl)COC(C)=O)OC(C)=O)=O

Description

This α-D-galactopyranosyl chloride derivative features a fully acetylated sugar backbone with a reactive anomeric chloride, enabling efficient glycosylation reactions. The acetamido group at C2 enhances stability and directs stereochemistry during coupling. Designed for synthetic glycochemistry workflows, it offers high reactivity under mild conditions with minimal epimerization.

Synthesis

  • Route1

    References

    • Traar, Pedro; Belaj, Ferdinand; Francesconi, Kevin A. Australian Journal of Chemistry, 2004 , vol. 57, # 11 p. 1051 - 1053
  • Route2

    References

    • Stokmaier, Daniela; Khorev, Oleg; Cutting, Brian; Born, Rita; Ricklin, Daniel; Ernst, Thomas O.G.; Boeni, Fabienne; Schwingruber, Kathrin; Gentner, Martin; Wittwer, Matthias; Spreafico, Morena; Vedani, Angelo; Rabbani, Said; Schwardt, Oliver; Ernst, Beat Bioorganic and Medicinal Chemistry, 2009 , vol. 17, # 20 p. 7254 - 7264
  • Route3
    • In-stock
      2-Acetamido-2-deoxy-D-glucopyranose|CS-0326546
      72-87-7
    • null|null
      75-36-5
    • ~52%
    • In-stock
      2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl chloride|CS-0098189
      41355-44-6

    References

    • ATOMIC ENERGY COUNCIL, INSTITUTE OF NUCLEAR ENERGY RESEARCH; LIU, SHOW-WEN; CHANG, YU; HSU, CHENG-FANG; TSAI, MING-CHE; CHIANG, TSUNG-HSIEN; DENG, YUEH-FENG; LU, KUEI-LIN; LIN, CHIH-YUAN; WANG, DA-MING; LI, CHING-YUN Patent: US2014/31533 A1, 2014 ; Location in patent: Paragraph 0096; 0097; 0098; 0099; 0100 ;

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-P280-P302+P352

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Computational Chemistry Data

  • TPSA   117.23
  • LogP   -0.1187
  • H_Acceptors   8
  • H_Donors   1
  • Rotatable_Bonds   5

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