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1-O-Acetyl-2,3,5-Tri-O-benzoyl-beta-D-Ribofuranose

  • CAS No. 6974-32-9

  • Cat. No. CS-W007928
  • Purity≥98%
  • MDL No.MFCD00005357

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

1-O-Acetyl-2,3,5-Tri-O-benzoyl-beta-D-Ribofuranose|CS-W007928

Structure of 6974-32-9

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General Information

  • CAS No. 6974-32-9
  • Cat. No. CS-W007928
  • Purity ≥98%
  • MDL No. MFCD00005357
  • Storage 4°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₂₈H₂₄O₉
  • Molecular Weight 504.48
  • Synonym(s) None
  • SMILES O=C(C1=CC=CC=C1)O[C@H]2[C@H]([C@@H](O[C@@H]2COC(C3=CC=CC=C3)=O)OC(C)=O)OC(C4=CC=CC=C4)=O

Description

1-O-Acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose serves as a key glycosyl donor in carbohydrate synthesis, featuring a protected ribose scaffold with orthogonal functional groups. The acetyl and benzoyl esters enable selective deprotection, while the β-configured anomeric center ensures stereospecific coupling. This derivative exhibits enhanced stability under standard conditions, facilitating reliable glycosylation reactions in complex oligosaccharide assembly.

Application

1-O-Acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose serves as a versatile nucleoside precursor, enabling efficient glycosylation reactions in the synthesis of antiviral and anticancer ribonucleoside analogs. Its protected hydroxyl groups exhibit high regioselectivity and stability under standard coupling conditions, facilitating clean assembly of complex sugar moieties. The acetyl and benzoyl protections provide excellent functional group tolerance and simplify purification, making it well-suited for bench-scale synthesis and process development.

Synthesis

  • Route1
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      115459-50-2
    • ~94%
    • In-stock
      1-O-Acetyl-2,3,5-Tri-O-benzoyl-beta-D-Ribofuranose|CS-W007928
      6974-32-9

    References

    • Zhengzhou University; Analyse Testing And Research Center Of Henan Province Patent: EP2177527 A1, 2010 ; Location in patent: Page/Page column 11 ;
  • Route2
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      22224-38-0
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      108-24-7
    • ~50%
    • In-stock
      1-O-Acetyl-2,3,5-Tri-O-benzoyl-beta-D-Ribofuranose|CS-W007928
      6974-32-9

    References

    • Banda, Geetha; Srinivasulu; Ugandhar; Chakravarthy Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006 , vol. 45, # 8 p. 1920 - 1923
  • Route3
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      52783-53-6
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      108-24-7
    • ~92%
    • In-stock
      1-O-Acetyl-2,3,5-Tri-O-benzoyl-beta-D-Ribofuranose|CS-W007928
      6974-32-9

    References

    • Kim, Myong Jung; Jeong, Lak Shin; Kim, Joong Hyup; Shin, Ji Hye; Chung, Soon Yong; Lee, Sang Kook; Chun, Moon Woo Nucleosides, Nucleotides and Nucleic Acids, 2004 , vol. 23, # 4 p. 715 - 724

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   114.43
  • LogP   3.5826
  • H_Acceptors   9
  • H_Donors   0
  • Rotatable_Bonds   8

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