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CS-W001157 4
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Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside

  • CAS No. 99409-32-2

  • Cat. No. CS-0098113
  • Purity≥97%
  • MDL No.None

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

Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside|CS-0098113

Structure of 99409-32-2

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General Information

  • CAS No. 99409-32-2
  • Cat. No. CS-0098113
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₂₂H₂₅NO₉S
  • Molecular Weight 479.50
  • Synonym(s) Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-b-D-thioglucopyranoside
  • SMILES O=C(C1=CC=CC=C1C2=O)N2[C@@H]3[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O[C@H]3SCC

Description

Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside serves as a key glycosylation donor in carbohydrate synthesis, featuring a β-configured thioglycoside linkage and phthalimido group that enhances anomeric control. The tri-O-acetyl protection pattern ensures compatibility with standard glycosylation conditions, while the ethyl ester facilitates purification and downstream manipulation. This derivative enables reliable access to complex oligosaccharides under mild activation protocols.

Application

Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside serves as a key glycosyl donor in stereoselective glycosylation reactions. The acetyl groups provide enhanced stability and solubility, while the phthalimido group at C-2 enables reliable stereocontrol during glycosidic bond formation. Its thioglycoside functionality facilitates activation under mild conditions, making it well-suited for complex oligosaccharide synthesis and modular building block applications in carbohydrate chemistry.

Synthesis

  • Route1

    References

    • Vesely, Jan; Ledvina, Miroslav; Jindrich, Jindrich; Saman, David; Trnka, Tomas Collection of Czechoslovak Chemical Communications, 2003 ,  vol. 68,  # 7  p. 1264 - 1274

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

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Computational Chemistry Data

  • TPSA   125.51
  • LogP   1.5557
  • H_Acceptors   10
  • H_Donors   0
  • Rotatable_Bonds   7

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