Cas no 14686-89-6 (1,2:5,6-Di-O-isopropylidene-a-D-gulofuranose)

1,2:5,6-Di-O-isopropylidene-α-D-gulofuranose is a protected sugar derivative widely used in synthetic organic chemistry and carbohydrate research. Its key advantages include enhanced stability due to the isopropylidene groups, which protect the hydroxyl functionalities from unwanted reactions while maintaining reactivity at the anomeric center. This compound serves as a versatile intermediate in the synthesis of nucleosides, glycosides, and other complex carbohydrates. Its crystalline form ensures high purity and ease of handling, making it suitable for precise stoichiometric applications. The rigid furanose ring structure also facilitates stereocontrol in subsequent transformations, underscoring its utility in asymmetric synthesis and pharmaceutical development.
1,2:5,6-Di-O-isopropylidene-a-D-gulofuranose structure
14686-89-6 structure
Product Name:1,2:5,6-Di-O-isopropylidene-a-D-gulofuranose
CAS No:14686-89-6
MF:C12H20O6
MW:260.283604621887
MDL:MFCD00005544
CID:138736
PubChem ID:11425442
Update Time:2025-10-31

1,2:5,6-Di-O-isopropylidene-a-D-gulofuranose Chemical and Physical Properties

Names and Identifiers

    • a-D-Gulofuranose,1,2:5,6-bis-O-(1-methylethylidene)-
    • 1,2:5,6-Di-O-isopropylidene-α-D-gulofuranose
    • (-)-1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE
    • 1,2,5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE
    • 1,2:5,6-DI-O-ISOPROPYLIDENE-A-D-GULOFURANOSE
    • Diacetone-D-Glucose
    • 1,2:5,6-Bis-O-(1-methylethylidene)-alpha-D-gulofuranose
    • GLUCOFURANOSE
    • DIACETONE-ALPHA-D-GLC
    • α-D-Gulose diacetonide
    • DIACETONE-ALPHA-D-GLUCOSE
    • DIISOPROPYLIDENEGLUCOFURANOSE
    • 1,2:5,6-Di-O-isopropylidene-α-D-gulose
    • 1,2,5,6-DI-O-ISO-PROPYLIDENEGLUCOFURANOSE
    • 1,2,5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-GULOSE
    • 1,2
    • 5,6-DI-O-ISOPROPYLIDENE-D-GLUCOFURANOSE
    • 1,2:5,6-DIISOPROPYLENE-ALPHA-D-GLUCOFURANOSE
    • (3aR,5R,6R,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol
    • DS-3320
    • A-D-gulofuranose
    • 1,2:5,6-Di-O-isopropylidene-I+/--D-gulofuranose
    • DTXSID301224246
    • alpha-D-Gulofuranose, 1,2:5,6-bis-O-(1-methylethylidene)-
    • (3aR,5R,6R,6aR)-5-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,2-d][1,3]dioxol-6-ol
    • SCHEMBL1847430
    • 1,2:5,6-Di-O-isopropylidene-alpha-D-gulofuranose
    • 14686-89-6
    • (3aR,5R,6R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol
    • 1,2:5,6-Di-O-isopropylidene-
    • CS-B1536
    • AKOS030241543
    • KEJGAYKWRDILTF-HOTMZDKISA-N
    • (3aR,5R,6R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol
    • 1,2:5,6-Bis-O-(1-methylethylidene)-I+/--D-gulofuranose
    • 1,2:5,6-Di-O-isopropylidene-a-D-gulofuranose
    • MDL： MFCD00005544
    • Inchi： 1S/C12H20O6/c1-11(2)14-5-6(16-11)8-7(13)9-10(15-8)18-12(3,4)17-9/h6-10,13H,5H2,1-4H3/t6-,7-,8+,9-,10-/m1/s1
    • InChI Key： KEJGAYKWRDILTF-HOTMZDKISA-N
    • SMILES： O1[C@H]2[C@@H]([C@@H]([C@@H]1[C@H]1COC(C)(C)O1)O)OC(C)(C)O2

Computed Properties

  • Exact Mass: 260.12600
  • Monoisotopic Mass: 260.126
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 6
  • Heavy Atom Count: 18
  • Rotatable Bond Count: 1
  • Complexity: 342
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 5
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 66.4A^2
  • XLogP3: 0

Experimental Properties

  • Color/Form: Gray white crystalline solid
  • Density: 1.214±0.06 g/cm3 (20 oC 760 Torr),
  • Melting Point: 105-106 oC
  • Boiling Point: 136.4±35.0 °C at 760 mmHg
  • Flash Point: 87.8±0.0 °C
  • Refractive Index: 1.483
  • Solubility: Slightly soluble (13 g/l) (25 o C),
  • PSA: 66.38000
  • LogP: 0.37520
  • Vapor Pressure: 9.2±0.2 mmHg at 25°C
  • Specific Rotation: -11 o (C=5, ETOH)

1,2:5,6-Di-O-isopropylidene-a-D-gulofuranose Security Information

1,2:5,6-Di-O-isopropylidene-a-D-gulofuranose Pricemore >>

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1,2:5,6-Di-O-isopropylidene-a-D-gulofuranose Production Method

1,2:5,6-Di-O-isopropylidene-a-D-gulofuranose Related Literature

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Additional information on 1,2:5,6-Di-O-isopropylidene-a-D-gulofuranose

1,2:5,6-Di-O-isopropylidene-a-D-gulofuranose (CAS No. 14686-89-6): A Comprehensive Overview

The compound 1,2:5,6-Di-O-isopropylidene-a-D-gulofuranose (CAS No. 14686-89-6) is a derivative of a-D-gulofuranose, a naturally occurring sugar. This compound has gained significant attention in the fields of organic chemistry and biochemistry due to its unique structural features and potential applications in drug design and material science. The isopropylidene groups attached to the sugar moiety introduce steric hindrance and rigidity, which can influence its reactivity and biological activity.

Recent studies have highlighted the importance of glycosylation in various biological processes, including cell signaling and immune responses. The a-D-gulofuranose backbone of this compound serves as a versatile platform for further chemical modifications. Researchers have explored the use of 1,2:5,6-Di-O-isopropylidene-a-D-gulofuranose in the synthesis of glycomimetics, which are compounds that mimic the structure and function of natural sugars. These glycomimetics have shown promise in inhibiting viral infections by targeting viral glycoproteins.

The synthesis of 1,2:5,6-Di-O-isopropylidene-a-D-gulofuranose typically involves protection-deprotection strategies to install the isopropylidene groups at specific positions on the sugar ring. This process requires precise control over stereochemistry to ensure the correct configuration of the final product. Advanced techniques such as enzymatic catalysis and microwave-assisted synthesis have been employed to improve the efficiency and scalability of this process.

In terms of applications, this compound has been utilized in the development of novel materials with tailored properties. For instance, its rigid structure makes it a potential candidate for use in supramolecular chemistry and self-assembling systems. Additionally, 1,2:5,6-Di-O-isopropylidene-a-D-gulofuranose has been investigated as a building block for creating biocompatible polymers and nanoparticles for drug delivery systems.

Recent research has also focused on the interaction of this compound with biological systems. Studies have demonstrated that its unique stereochemistry can modulate its binding affinity to specific proteins and enzymes. This property makes it a valuable tool in studying sugar-protein interactions and developing new therapeutic agents.

Furthermore, the isopropylidene groups in this compound provide opportunities for additional functionalization. Chemists have explored the use of click chemistry and other orthogonal reactions to attach various functionalities to this sugar derivative. These modifications can enhance its bioavailability or enable its use in diagnostic applications.

In conclusion, 1,2:5,6-Di-O-isopropylidene-a-D-gulofuranose (CAS No. 14686-89-6) is a versatile compound with significant potential in multiple fields. Its unique structure and reactivity make it an attractive target for both fundamental research and applied development. As our understanding of its properties continues to grow, so too does its potential to contribute to advancements in medicine, materials science, and beyond.

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