Cas no 3616-19-1 (D-(+)-Cellobiose Octaacetate)

D-(+)-Cellobiose Octaacetate is a fully acetylated derivative of cellobiose, a disaccharide composed of two β-D-glucose units linked by a β(1→4) bond. This crystalline compound is widely used as an intermediate in organic synthesis, particularly in carbohydrate chemistry, due to its stability and solubility in common organic solvents. Its octaacetyl structure makes it a valuable precursor for glycosylation reactions and the preparation of modified saccharides. The high purity and well-defined stereochemistry of D-(+)-Cellobiose Octaacetate ensure reproducibility in research and industrial applications, such as polymer science and pharmaceutical development. Its consistent performance and ease of handling further enhance its utility in synthetic workflows.
D-(+)-Cellobiose Octaacetate structure
D-(+)-Cellobiose Octaacetate structure
Product Name:D-(+)-Cellobiose Octaacetate
CAS No:3616-19-1
MF:C28H38O19
MW:678.5899310112
CID:296081
PubChem ID:107429
Update Time:2025-05-22

D-(+)-Cellobiose Octaacetate Chemical and Physical Properties

Names and Identifiers

    • D-Glucopyranose,4-O-(2,3,4,6-tetra-O-acetyl-b-D-glucopyranosyl)-, 1,2,3,6-tetraacetate
    • ALPHA-D-CELLOBIOSE OCTAACETATE
    • D-(+)-Cellobiose Octaacetate
    • D-Cellobiose octaacetate
    • D-β-Octaacetocellobiose
    • 1,2,3,5-tetrazin
    • D-&#946
    • -Octaacetocellobiose
    • Cellobiose octaacetate
    • (2S,3R,4S,5R,6R)-6-(acetoxymethyl)-5-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yloxy)tetrahydro-2H-pyran-2,3,4-triyl triacetate
    • AS-11695
    • AM83980
    • NS00082827
    • [(2R,3R,4S,5R)-4,5,6-triacetyloxy-3-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
    • beta -D-Maltose octaacetate
    • 20764-63-0
    • A-D-Cellobiose octaacetate
    • D(+)-Cellobiose octaacetate
    • Maybridge1_004250
    • C-2650
    • SCHEMBL181128
    • AMY32650
    • AKOS016010485
    • (2S,3R,4S,5R,6R)-6-(acetoxymethyl)-5-(((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2,3,4-triyl triacetate
    • EINECS 222-799-7
    • 3616-19-1
    • D-Glucopyranose, 4-O-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-, tetraacetate
    • HMS553J06
    • Beta-D-maltose octaacetate
    • 22352-19-8
    • [(2R,3R,4S,5R,6S)-4,5,6-triacetyloxy-3-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
    • 20880-60-8
    • CS-W014412
    • 1,2,2',3,3',4',6,6'-OCTA-O-ACETYL-BETA MALTOSE
    • MFCD00009600
    • D-Glucopyranose, 4-O-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-, 1,2,3,6-tetraacetate
    • 5346-90-7
    • Octa-O-acetyl D-Cellobiose
    • Inchi: 1S/C28H38O19/c1-11(29)37-9-19-21(39-13(3)31)23(40-14(4)32)26(43-17(7)35)28(46-19)47-22-20(10-38-12(2)30)45-27(44-18(8)36)25(42-16(6)34)24(22)41-15(5)33/h19-28H,9-10H2,1-8H3/t19-,20-,21-,22-,23+,24+,25-,26-,27-,28+/m1/s1
    • InChI Key: WOTQVEKSRLZRSX-HYSGBLIFSA-N
    • SMILES: O([C@H]1[C@@H]([C@H]([C@@H]([C@@H](COC(C)=O)O1)OC(C)=O)OC(C)=O)OC(C)=O)[C@@H]1[C@@H](COC(C)=O)O[C@H]([C@@H]([C@H]1OC(C)=O)OC(C)=O)OC(C)=O

Computed Properties

  • Exact Mass: 678.20100
  • Monoisotopic Mass: 678.200729
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 19
  • Heavy Atom Count: 47
  • Rotatable Bond Count: 20
  • Complexity: 1200
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 10
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 0.2
  • Topological Polar Surface Area: 238

Experimental Properties

  • Density: 1.37±0.1 g/cm3 (20 oC 760 Torr),
  • Melting Point: 227-228 oC
  • Boiling Point: 683.1°Cat760mmHg
  • Flash Point: 281.2°C
  • Refractive Index: 1.507
  • Solubility: Slightly soluble (3.3 g/l) (25 o C),
  • Stability/Shelf Life: Stable at RT
  • PSA: 238.09000
  • LogP: -0.83080

D-(+)-Cellobiose Octaacetate Security Information

D-(+)-Cellobiose Octaacetate Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
TRC
C255025-5g
D-(+)-Cellobiose Octaacetate
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$ 161.00 2023-09-08
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Additional information on D-(+)-Cellobiose Octaacetate

Recent Advances in the Study of D-(+)-Cellobiose Octaacetate (CAS: 3616-19-1) in Chemical Biology and Pharmaceutical Research

D-(+)-Cellobiose Octaacetate (CAS: 3616-19-1) is a chemically modified derivative of cellobiose, where all eight hydroxyl groups are acetylated. This compound has garnered significant attention in recent years due to its versatile applications in chemical biology, drug delivery, and material science. Recent studies have explored its potential as a chiral building block, a biodegradable polymer precursor, and a carrier for targeted drug delivery systems. This research brief synthesizes the latest findings on D-(+)-Cellobiose Octaacetate, highlighting its molecular properties, synthetic pathways, and emerging applications in pharmaceutical sciences.

One of the most notable advancements in the study of D-(+)-Cellobiose Octaacetate is its role in the development of biodegradable polymers. A 2023 study published in Biomacromolecules demonstrated that this compound can serve as a monomer for synthesizing polyesters with tunable degradation rates, making it a promising candidate for environmentally friendly packaging materials and medical implants. The researchers utilized a novel enzymatic polymerization technique, which significantly improved the yield and purity of the resulting polymers compared to traditional chemical methods.

In the realm of drug delivery, D-(+)-Cellobiose Octaacetate has shown exceptional promise as a carrier for hydrophobic drugs. A recent Journal of Controlled Release article (2024) detailed its use in formulating nanoparticles that enhance the solubility and bioavailability of poorly water-soluble anticancer agents. The study reported a 40% increase in drug loading capacity and a sustained release profile over 72 hours, attributed to the compound's unique acetylated structure. These findings suggest that D-(+)-Cellobiose Octaacetate could revolutionize the delivery of chemotherapeutic drugs, minimizing side effects and improving patient outcomes.

Another groundbreaking application of D-(+)-Cellobiose Octaacetate lies in its use as a chiral auxiliary in asymmetric synthesis. Researchers at ETH Zurich (2023) developed a highly enantioselective glycosylation reaction using this compound as a template, achieving up to 98% enantiomeric excess for complex carbohydrate derivatives. This methodology opens new avenues for the synthesis of biologically active compounds, including antibiotics and antiviral agents, with precise stereochemical control.

Despite these promising developments, challenges remain in the large-scale production and purification of D-(+)-Cellobiose Octaacetate. A 2024 review in Organic Process Research & Development highlighted the need for more efficient acetylation protocols and greener solvents to improve the sustainability of its synthesis. Future research directions may focus on biocatalytic approaches and flow chemistry techniques to address these limitations while maintaining high product quality.

In conclusion, D-(+)-Cellobiose Octaacetate (CAS: 3616-19-1) represents a multifaceted compound with growing importance in pharmaceutical and materials research. Its unique chemical properties continue to inspire innovative applications, from advanced drug delivery systems to sustainable polymers. As synthetic methodologies evolve and our understanding of its biological interactions deepens, this compound is poised to play an increasingly vital role in addressing pressing challenges in healthcare and environmental sustainability.

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