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CS-W001157 4
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4-Methylphenyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside

  • CAS No. 28244-94-2

  • Cat. No. CS-0098063
  • Molecule weight454.49
  • Purity≥98%
  • MDL No.None

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

4-Methylphenyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside|CS-0098063

Structure of 28244-94-2

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General Information

  • CAS No. 28244-94-2
  • Cat. No. CS-0098063
  • Purity ≥98%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₂₁H₂₆O₉S
  • Molecular Weight 454.49
  • Synonym(s) 4-Methylphenyl 2,3,4,6-tetra-O-acetyl-1-thio-b-D-glucopyranoside
  • SMILES CC(C=C1)=CC=C1S[C@H]2[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O2

Description

This thio-glycoside delivers a stable, electron-rich glycosyl donor with enhanced solubility in organic solvents. The tetra-O-acetyl protection pattern ensures controlled reactivity, while the 4-methylphenyl aglycon facilitates purification and handling. Ideal for stereoselective glycosylation under mild conditions.

Application

4-Methylphenyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside serves as a robust glycosyl donor for stereoselective glycosylation reactions. The fully acetylated sugar moiety enhances solubility and stability, while the β-configured thio-glycoside enables reliable activation under mild conditions. It functions effectively in standard coupling protocols, facilitating the construction of complex oligosaccharides and glycoconjugates with high anomeric control.

Safety Information

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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   114.43
  • LogP   2.17022
  • H_Acceptors   10
  • H_Donors   0
  • Rotatable_Bonds   7

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