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104013-04-9, Tetra-O-acetyl-3-chloro-3-deoxy-D-glucopyranose, CAS:104013-04-9

104013-04-9, Tetra-O-acetyl-3-chloro-3-deoxy-D-glucopyranose,
C14H19ClO9 / 366.747



1,2,4,6-Tetra-O-acetyl-3-chloro-3-deoxy-D-glucopyranose, also known as "Tetra-acetyl-3-chloro-3-deoxy-D-glucose," is a synthetic carbohydrate intermediate that is commonly used in the chemical synthesis of oligosaccharides and glycosides. The compound was first synthesized by Chugaev in 1912, and since then, it has been widely used as a protective agent for hydroxyl groups during glycosylation reactions.

Synthesis and Characterization:

There are several methods for synthesizing Tetra-acetyl-3-chloro-3-deoxy-D-glucose, but the most popular one is the direct acetylation of 3-chloro-3-deoxy-D-glucose with acetic anhydride and catalytic amounts of a Lewis acid, such as zinc chloride or tin chloride. The reaction is carried out under reflux in anhydrous conditions to prevent hydrolysis. The product is purified by recrystallization from a mixture of ethanol and ether.

The compound is characterized by various spectroscopic techniques, such as NMR, IR, and MS. The NMR spectrum shows five signals at δ 2.08, 2.24, 2.31, 2.43, and 2.75 ppm, corresponding to the acetyl groups. The chloro group appears at δ 4.8 ppm. The IR spectrum shows characteristic stretching bands for carbonyl (C=O) and ether (C-O) groups. The MS spectrum shows a molecular ion peak at m/z 353, indicating the presence of one acetyl group.

Analytical Methods:

There are several analytical methods for quantifying Tetra-acetyl-3-chloro-3-deoxy-D-glucose in various matrices, such as reaction mixtures, crude products, and biological samples. One of the most popular methods is high-performance liquid chromatography (HPLC) with UV detection at 254 nm. The compound has a high molar absorptivity (ε) and a good retention time on reversed-phase columns. The method is sensitive, specific, and reproducible.

Biological Properties:

There are limited studies on the biological properties of Tetra-acetyl-3-chloro-3-deoxy-D-glucose, but some evidence suggests that it may have immunomodulatory and antitumor activities. The compound has been shown to enhance the production of interleukin-2 (IL-2) and interferon gamma (IFN-γ) by human T cells in vitro, indicating a potential role in cancer immunotherapy. Moreover, the compound has been incorporated into tumor-targeting glycoconjugates and liposomes, leading to enhanced anticancer efficacy in animal models.

Toxicity and Safety in Scientific Experiments:

The toxicity and safety of Tetra-acetyl-3-chloro-3-deoxy-D-glucose depend on the dose and route of administration. The compound is non-flammable, non-explosive, and non-irritating to the skin and eyes. However, it may cause respiratory and gastrointestinal irritation if inhaled or ingested. Moreover, the compound may decompose under acidic or basic conditions, leading to the release of toxic gases, such as hydrogen chloride and acetic acid. Therefore, proper handling and disposal of the compound are necessary to avoid health and environmental hazards.

Applications in Scientific Experiments:

Tetra-acetyl-3-chloro-3-deoxy-D-glucose has numerous applications in scientific experiments, especially in the field of carbohydrate chemistry. The compound is used as a protective agent for hydroxyl groups during glycosylation reactions, allowing for selective and efficient synthesis of oligosaccharides and glycosides. Moreover, the compound is used as a building block for the synthesis of chitin, chitosan, and other biopolymers. Additionally, the compound is used as a non-toxic substitute for phosgene in the synthesis of isocyanates and carbamates.

Current State of Research:

The current state of research on Tetra-acetyl-3-chloro-3-deoxy-D-glucose is diverse and active. On one hand, the compound is still used as a crucial reagent in carbohydrate chemistry, and new methods for its synthesis and characterization are continuously developed. On the other hand, the compound is explored for its potential biotechnological and biomedical applications, such as immunotherapy, drug delivery, and biodegradable materials. Moreover, the compound is examined for its safety and environmental impact, and new regulations and guidelines for its handling and disposal are proposed.

Potential Implications in Various Fields of Research and Industry:

Tetra-acetyl-3-chloro-3-deoxy-D-glucose has potential implications in various fields of research and industry, such as:

a. Carbohydrate chemistry: The compound can be used to synthesize various biologically relevant oligosaccharides and glycosides, which can be utilized as vaccines, therapeutics, and biomaterials.

b. Biotechnology: The compound can be used as a scaffold for the synthesis of novel glycoconjugates with enhanced bioactivity and specificity.

c. Biomedical engineering: The compound can be incorporated into drug delivery systems, such as nanoparticles and liposomes, to enhance their efficacy and targeting.

d. Environmental science: The compound can be used as a safer alternative to phosgene in the synthesis of isocyanates, which are widely used in the production of polyurethane foams, coatings, and adhesives.

10. Limitations and Future Directions:

There are several limitations and future directions for the research on Tetra-acetyl-3-chloro-3-deoxy-D-glucose, such as:

a. Toxicity and safety issues: Further studies are needed to evaluate the toxicity and safety of the compound under different conditions and in various organisms, including humans.

b. Biocompatibility and biodegradability: Further studies are needed to investigate the biocompatibility and biodegradability of the compound and its derivatives in vivo, especially in the context of drug delivery and tissue engineering.

c. Chemical stability and reactivity: Further studies are needed to explore the chemical stability and reactivity of the compound under different pH, temperature, and pressure conditions, as well as in the presence of other reagents and catalysts.

d. Scale-up and cost-effectiveness: Further studies are needed to develop scalable and cost-effective methods for the synthesis and purification of the compound, as well as its derivatives and conjugates, to facilitate their industrial and clinical applications.

CAS Number104013-04-9
Product Name1,2,4,6-Tetra-O-acetyl-3-chloro-3-deoxy-D-glucopyranose
IUPAC Name[(2R,3R,4S,5S)-3,5,6-triacetyloxy-4-chlorooxan-2-yl]methyl acetate
Molecular FormulaC14H19ClO9
Molecular Weight366.747
Synonyms3-Chloro-3-deoxy-D-glucopyranose Tetraacetate;

CAS No: 104013-04-9 Synonyms: 3-Chloro-3-deoxy-1,2,4,6-tetra-O-acetyl-D-glucopyranose  MDL No: MFCD03425532 Chemical Formula: C14H19ClO9 Molecular Weight: 366.747


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