CAS · 572-09-8
Product Overview
2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide is a high-purity nucleosides-nucleotides supplied for industrial and specialty chemical applications. Contact our team for specifications, packaging options and lead times.
Product Specifications
| Property | Specification |
|---|---|
| Appearance | Off-white to white powder |
| Purity (HPLC) | 98% min |
| ¹H NMR (CDCl₃) | Conforms to structure |
| Specific Optical Rotation [α]D²⁰ (c=3 in CHCl₃) | +196° to +200° |
| Water (K.F.) | 0.5% max |
Applications
1. Glycosylation Reagent (Donor)
● Used as a glycosyl donor in the formation of glycosidic bonds.
● Reacts with alcohols, thiols, or amines (glycosyl acceptors) under acidic or Lewis acid catalysis to form glycosides.
● Important in the stepwise synthesis of oligosaccharides, which are critical in biological recognition processes.
2. Carbohydrate and Glycomimetic Synthesis
● Employed in synthesizing glycomimetics, glycolipids, glycosylated natural products, and biologically active oligosaccharides.
● Useful in pharmaceutical chemistry for the development of carbohydrate-based drugs or drug delivery systems.
3. Chemical Biology and Glycobiology
● Supports the synthesis of probes and ligands to study lectins, enzymes, and glycosyltransferases.
● Used in designing multivalent glycoconjugates for research in cell adhesion, pathogen binding, and immune response mechanisms.
4. Intermediate for Modified Sugars
● Acts as a building block for modified glucose derivatives, including fluorinated, azido, or sulfur-substituted analogs, which are useful in metabolic labeling and bioconjugation.
Benefits
1. High Reactivity and Selectivity
● The bromide at the anomeric center allows for efficient activation under mild conditions (e.g., with silver salts, Lewis acids like BF₃·Et₂O), providing high glycosylation yields.
● The acetyl protecting groups improve solubility and prevent side reactions at other hydroxyl sites, enhancing regioselectivity.
2. Versatility
● Compatible with a wide range of glycosyl acceptors and reaction conditions.
● Used across diverse synthetic strategies including block synthesis and iterative chain elongation in carbohydrate assembly.
3. Commercial Availability and Accessibility
● Readily available and used extensively in research labs, particularly in glycoscience, medicinal chemistry, and synthetic organic chemistry.
Conclusion
2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide丨CAS 572-09-8 is a cornerstone reagent in the synthesis of glycosidic linkages and complex carbohydrate structures. Its balance of reactivity, selectivity, and ease of use makes it a go-to compound for researchers in the fields of glycochemistry, drug development, and bioconjugation. Whether used in assembling therapeutic oligosaccharides or designing glycoconjugate vaccines, this brominated sugar derivative remains indispensable in modern organic synthesis.
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