Overview
1,3,4,6-Tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose is a specialized carbohydrate derivative that serves as a crucial intermediate in synthetic carbohydrate chemistry. The compound features acetyl protecting groups at multiple hydroxyl positions and a trichloroethoxycarbonyl (Troc) protected amino group at the 2-position, making it particularly valuable for controlled glycosylation reactions. Its molecular architecture allows for selective deprotection strategies, enabling the synthesis of complex oligosaccharides with precise stereochemistry. This compound has gained significant importance in pharmaceutical research due to its utility in creating glycosylated drug candidates and investigating carbohydrate-protein interactions. The Troc protecting group offers stability during synthetic manipulations while being removable under mild conditions, making this derivative a preferred choice for multistep synthetic routes in medicinal chemistry applications.
Physical and Chemical Properties
The compound presents as a white to off-white crystalline powder with moderate stability under standard laboratory conditions. Its molecular weight of 470.66 g/mol reflects the substantial mass contributed by the multiple acetyl groups and the trichloroethoxycarbonyl moiety. The melting point typically ranges between 150-155°C, though this may vary slightly depending on crystallization conditions and purity. Solubility characteristics show preferential dissolution in chlorinated solvents such as dichloromethane and chloroform, with moderate solubility in acetone and limited solubility in alcohols. The acetyl groups confer significant lipophilicity, while the Troc-protected amine provides both steric bulk and electronic effects that influence reactivity. The compound demonstrates stability in neutral to slightly acidic conditions but may undergo decomposition under strongly basic or reducing environments.
Main Applications
This acetylated glucopyranose derivative finds extensive use as a building block in the synthesis of complex oligosaccharides and glycoconjugates. Its protected amino group allows for controlled glycosylation reactions essential for creating structurally defined carbohydrate moieties in drug development. Pharmaceutical researchers particularly value this compound for constructing glycosylated natural products and investigating carbohydrate-based biological recognition processes. In industrial applications, the compound serves as a key intermediate for producing carbohydrate-based vaccines and therapeutic agents targeting infectious diseases and cancer. The Troc protecting group's orthogonal reactivity enables sequential synthetic strategies, making this derivative valuable for automated oligosaccharide synthesis platforms. Recent advances have also demonstrated its utility in creating carbohydrate arrays for high-throughput screening of biological interactions.
Safety and Storage
Proper handling of this chemical requires standard laboratory precautions including the use of gloves, protective eyewear, and adequate ventilation. The compound may cause irritation upon contact with skin or eyes, and inhalation of dust should be avoided. In case of exposure, affected areas should be flushed with copious amounts of water, and medical attention sought if irritation persists. For optimal stability, the material should be stored in tightly sealed containers under inert atmosphere at 2-8°C. Long-term storage benefits from the inclusion of desiccant packets to prevent moisture absorption. The compound shows reasonable thermal stability but should be protected from extreme heat and direct sunlight. Material safety data sheets should be consulted for detailed handling procedures and emergency response measures specific to this chemical.
B2B Procurement Guide
When sourcing this specialized carbohydrate derivative, buyers should verify the supplier's analytical documentation including HPLC purity certificates and NMR characterization data. Typical commercial offerings range from 95% to 99% purity, with higher purity grades commanding premium pricing. Procurement specialists should confirm batch-to-batch consistency through COA review, paying particular attention to water content and residual solvent levels. Lead times for custom synthesis can range from 4-8 weeks depending on quantity and purity requirements. For research-scale quantities (1-10g), inventory items are often available from specialty chemical distributors. Bulk procurement (100g+) may require direct engagement with synthetic chemistry manufacturers capable of multi-step organic synthesis under GMP-like conditions. Pricing shows significant volume discounts, with kilogram-scale purchases typically offering 30-50% cost reduction per gram compared to research quantities.
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