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1,2-O-Isopropylidene-alpha-d-glucofuranose

  • CAS No. 18549-40-1

  • Cat. No. CS-0128848
  • Purity≥98%
  • MDL No.MFCD00063244

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

1,2-O-Isopropylidene-alpha-d-glucofuranose|CS-0128848

Structure of 18549-40-1

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General Information

  • CAS No. 18549-40-1
  • Cat. No. CS-0128848
  • Purity ≥98%
  • MDL No. MFCD00063244
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₆O₆
  • Molecular Weight 220.22
  • Synonym(s) Mono-acetone glucose; 1,2-O-Isopropylidene-α-D-glucofuranose
  • SMILES O[C@@H]1[C@]2([H])[C@](OC(C)(O2)C)([H])O[C@]1([H])[C@H](O)CO

Description

This protected glucose derivative features a stable acetonide ring that locks the furanose form, enhancing shelf life and simplifying handling. The rigid structure facilitates selective glycosylation reactions in carbohydrate synthesis, serving as a reliable building block for complex oligosaccharides.

Synthesis

  • Route1
    • null|null
      499139-11-6
    • ~61%
    • In-stock
      1,2-O-Isopropylidene-alpha-d-glucofuranose|CS-0128848
      18549-40-1

    References

    • Markovic, Dean; Vogel, Pierre Organic Letters, 2004 , vol. 6, # 16 p. 2693 - 2696
  • Route2

    References

    • Silva, Sandrina; Sanchez-Fernandez, Elena M.; Ortiz Mellet, Carmen; Tatibouet, Arnaud; Pilar Rauter, Amelia; Rollin, Patrick European Journal of Organic Chemistry, 2013 , # 35 p. 7941 - 7951
  • Route3
    • (3AR,5R,6S,6aR)-5-((R)-1-hydroxy-2-(trityloxy)ethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol|CS-0516544
      33737-08-5
    • ~93%
    • In-stock
      1,2-O-Isopropylidene-alpha-d-glucofuranose|CS-0128848
      18549-40-1

    References

    • Wu, Qinpei; Wang, Yuan; Chen, Wei; Liu, Hua Synthetic Communications, 2006 , vol. 36, # 10 p. 1361 - 1366

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   88.38
  • LogP   -1.4231
  • H_Acceptors   6
  • H_Donors   3
  • Rotatable_Bonds   2

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