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Tri-O-Acetyl-D-Glucal

    • Product Name Tri-O-Acetyl-D-Glucal
    • Alias 1,2,3-Tri-O-acetyl-α-D-glucal
    • Einecs 256-973-3
    • Mininmum Order 1 g
    • Factory Site Tengfei Creation Center,55 Jiangjun Avenue, Jiangning District,Nanjing
    • Price Inquiry admin@sinochem-nanjing.com
    • Manufacturer Sinochem Nanjing Corporation
    • CONTACT NOW
    VTB
    Specifications

    HS Code

    180498

    Cas Number 77711-39-6
    Molecular Formula C12H16O8
    Molecular Weight 288.25 g/mol
    Iupac Name 1,2,3-Tri-O-acetyl-D-glucal
    Appearance White to off-white solid
    Purity Typically ≥98%
    Melting Point 102-104°C
    Solubility Soluble in common organic solvents (e.g., dichloromethane, ethanol)
    Storage Temperature 2-8°C
    Synonyms Triacetyl-D-glucal; 1,2,3-Tri-O-acetyl-D-glucal
    Smiles CC(=O)O[C@@H]1OC=C(CO[C@@H]1OC(=O)C)OC(=O)C
    Inchi InChI=1S/C12H16O8/c1-5(13)16-9-7(18-11(3)15)4-8(19-12(4,17)14)20-10(9)6(2)11/h4,9-10,14H,1-3H3

    As an accredited Tri-O-Acetyl-D-Glucal factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.

    Packing & Storage
    Packing Tri-O-Acetyl-D-Glucal is packaged in a 25-gram amber glass bottle with a secure screw cap and detailed labeling.
    Shipping Tri-O-Acetyl-D-Glucal is shipped in a tightly sealed container under ambient conditions. It should be protected from moisture, excessive heat, and direct sunlight. Standard chemical transport regulations apply, and documentation for safe handling and compliance with local and international shipping guidelines will be included with the package.
    Storage Tri-O-Acetyl-D-Glucal should be stored in a cool, dry, and well-ventilated area, away from moisture and incompatible materials such as strong acids or bases. Keep the container tightly sealed and protect it from direct sunlight. Ideally, store at a temperature between 2–8°C (refrigerator). Ensure storage conditions prevent hydrolysis, and follow standard chemical storage safety protocols.
    Application of Tri-O-Acetyl-D-Glucal

    Applications of Tri-O-Acetyl-D-Glucal in Industrial Manufacturing

    Tri-O-Acetyl-D-Glucal serves as an essential building block in specialty carbohydrate chemistry, supporting various advanced organic synthesis workflows across multiple high-value industries. Below, we focus exclusively on real-world downstream applications where this intermediate delivers specific performance outcomes, process efficiencies, and regulatory-compliant solutions.

    1. Nucleoside and Nucleotide Pharmaceutical Intermediate Synthesis

    Tri-O-Acetyl-D-Glucal features prominently in the efficient production of modified nucleosides and nucleotides that act as active pharmaceutical ingredients (APIs) for antiviral, anticancer, and genetic medicine therapies. Pharmaceutical manufacturers utilize its protected glucal structure for stereoselective glycosylation, minimizing by-products and simplifying purification steps. The acetyl-protected framework facilitates precise control over glycosidic bond formation, which is central to high-quality, compliant supply of molecular building blocks for finished drugs.

    Industry compliance standards

    • ICH Q7 Good Manufacturing Practice for Active Pharmaceutical Ingredients (APIs)
    • USP–NF Monographs for Nucleoside/Nucleotide APIs
    • EU EudraLex Volume 4 GMP Guidelines
    • FDA 21 CFR Part 211 (finished pharmaceuticals)

    Typical usage ratio

    • Ranges from 1.2 to 2.5 equivalents relative to aglycone acceptors, based on coupling protocol and desired yield optimization during glycosylation.

    Downstream process integration

    • Added at the glycosyl donor stage under Lewis acid or metal-catalyzed conditions to couple with heterocyclic bases or pre-functionalized acceptors in anhydrous organic media.

    Final product types

    • Antiviral nucleoside drug substances (e.g., cytidine and uridine analogs)
    • Anticancer nucleotide analogs
    • Oligonucleotide intermediates for genetic medicines
    • Prodrug synthesis intermediates

    2. Carbohydrate-Based Vaccine Antigen Synthesis

    Esteemed biopharmaceutical groups employ Tri-O-Acetyl-D-Glucal for controlled synthesis of defined carbohydrate antigens. This intermediate supports construction of glycan structures essential for conjugate vaccine programs targeting infectious diseases. Its use ensures robust acetylated glycoside protection, facilitating downstream deprotection, site-selective functionalization, and attachment to carrier proteins. Purity and batch consistency remain critical for regulatory acceptance in vaccine ingredient supply chains.

    Industry compliance standards

    • WHO Technical Report Series on the Quality Control of Vaccines
    • ICH Q11 Development and Manufacture of Drug Substances
    • Ph. Eur. Monographs for Carbohydrate Vaccine Components
    • US FDA CBER guidelines for biologics

    Typical usage ratio

    • Approximately 1.1 to 1.5 molar equivalents per glycosylation event, adjusted per carbohydrate chain length and antigen complexity.

    Downstream process integration

    • Introduced during orthogonal protecting group strategy deployment at the oligosaccharide chain assembly phase, prior to conjugation with carrier proteins or adjuvants.

    Final product types

    • Glycoconjugate vaccine antigen chains
    • Bacterial polysaccharide vaccine intermediates
    • Synthetic oligosaccharide mimetics for immunotherapy
    • Protein-carbohydrate conjugates

    3. Chiral Auxiliary in Fine Chemical Synthesis

    Advanced organic synthesis operations make use of Tri-O-Acetyl-D-Glucal’s defined stereochemistry as a chiral auxiliary or precursor, particularly in constructing structural motifs for fragrances, flavors, and specialty agrochemicals. The unique π–glycal system enables enantioselective transformations and cycloaddition reactions, helping downstream formulators maximize yield of high-value, chiral fine chemicals. Rigorous quality management of this stage supports downstream batch traceability and product documentation.

    Industry compliance standards

    • ISO 9001:2015 Quality Management Systems
    • REACH Regulation (EC) No 1907/2006 for chemical safety
    • IFRA Standards for Fragrance Ingredients
    • FAO/WHO Specifications for Agrochemical Intermediates

    Typical usage ratio

    • Usually 1.0 mol equivalent as chiral auxiliary per transformation; can vary from 0.8 to 1.5 depending on reaction selectivity and scale.

    Downstream process integration

    • Employed during enantioselective cycloaddition, Michael addition, or C–C bond forming reactions in custom synthesis routes for chiron-based ingredients.

    Final product types

    • Chiral fragrance additives (e.g., macrocyclic musks)
    • Chiral flavoring compounds
    • Agrochemical lead structures
    • Enantio-enriched specialty chemical intermediates

    4. Glycosyl Donor for Specialty Polymer Modification

    Manufacturers specializing in biocompatible and functionalized polymers turn to Tri-O-Acetyl-D-Glucal as a controlled glycosyl donor for post-polymerization glycosylation. This feedstock introduces carbohydrate motifs, enhancing biocompatibility, cellular recognition or hydrophilicity in engineered polymer matrices. Its integration permits straightforward acetyl removal and further chemical modification to tailor final polymer attributes by customer specification.

    Industry compliance standards

    • ISO 13485:2016 (Medical Devices – Quality Management Systems, for polymeric biomaterials)
    • FDA Guidance for Industry: Biocompatibility Evaluation of Medical Device Polymers
    • RoHS 2011/65/EU for restricted hazardous substances (electronics encapsulation)
    • REACH Annex XVII restrictions for functionalized chemicals

    Typical usage ratio

    • 0.5% to 2% by weight relative to total polymer matrix, selected based on target surface density of glycosylation and desired end application.

    Downstream process integration

    • Introduced post-polymerization via hydrazinolysis or acid-catalyzed glycosylation, often in organic-aqueous co-solvent systems compatible with medical or specialty device manufacturing.

    Final product types

    • Biocompatible coatings for medical devices
    • Cell-adhesion-promoting hydrogels
    • Functional polymer scaffolds for tissue engineering
    • Diagnostic microarray substrates
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    Certification & Compliance
    More Introduction

    Tri-O-Acetyl-D-Glucal: Practical Insights From the Lab Floor

    A Closer Look at One of Our Core Fine Chemicals

    Every batch of Tri-O-Acetyl-D-Glucal that leaves our facility tells a story about precision, responsibility, and hands-on know-how. Over decades of direct production experience, certain compounds stand out for their versatility and reliability. Tri-O-Acetyl-D-Glucal (Triacetyl-D-Glucal) belongs in this category. Its structure, rooted in D-glucal acetylation, helps drive results in both research and intermediate manufacturing processes. Unlike many specialty chemicals that drift in and out of fashion, demand for high-grade Tri-O-Acetyl-D-Glucal persists. We’ve seen researchers across the globe lean on it to build advanced carbohydrates, design glycosylation projects, and streamline the synthesis of bioactive molecules. Our history with this compound includes countless process refinements, pilot-scale runs, and quality-control challenges met head-on by lab teams and production engineers working together in real time.

    Product Model and Key Specifications in Practice

    Our Tri-O-Acetyl-D-Glucal, known as Model TA-DG-101 in our inventory, gets attention not based on model number but rather on how it performs in the lab. Throughout years of batch production, quality has come to mean more than paperwork. What our chemists and production supervisors notice most is ease of handling and purity. Each drum passes internal HPLC tests—material with over 98% purity hits the mark for most applications. This is not a theoretical number pulled from technical literature; it’s a benchmark that comes straight from collecting samples, running analytics, and verifying consistent acetylation across the molecule.

    Moisture sensitivity affects acetylated sugars, so we operate under nitrogen for critical steps, and our drying protocols are not “suggestions”—they’re logged, timestamped, and checked. Handling characteristics, such as flow and dusting, depend on controlled granulation and careful packing. Our team pays close attention to the color and appearance: the off-white, crystalline powder with a slight sheen signals clean processing without thermal degradation. Stability is another topic with real consequences for researchers: we seal product in airtight bags inside lined drums and store in a temperature-controlled warehouse. Years of feedback have taught us which shipments might face humidity spikes or long customs delays, so we reinforce packaging for those markets. This ongoing dialogue between production, QC, and customers shapes our approach far more than any marketing presentation could.

    Real-World Uses and What Sets Tri-O-Acetyl-D-Glucal Apart

    Tri-O-Acetyl-D-Glucal rarely travels alone on a lab bench. Teams synthesize oligosaccharides, glycosides, and modified carbohydrates; those reactions perform better with a trusted source of core intermediates. The value of Tri-O-Acetyl-D-Glucal lies in the high selectivity its acetyl groups offer during protection and deprotection strategies. In contrast to simpler acetylated sugars, this compound can serve as both a key intermediate and as a starting point for a broader range of transformations. We’ve watched process chemists push reaction conditions further, taking advantage of its unique reactivity—leaving group ability is strong enough to enable downstream glycosylation, yet the molecule avoids the fussiness of more delicate sugar-protected forms.

    Academic laboratories often design new glycosidic bonds while industrial teams rely on scale-up runs for pharmaceutical and fine chemical synthesis. One researcher may use a handful of grams to map out a mechanism, while another group orders multi-kilo lots to prepare precursors for enzyme inhibitors, antivirals, or other active pharmaceutical ingredients. Throughout these runs, a common refrain emerges: Tri-O-Acetyl-D-Glucal saves steps. Its predictable response to both acidic and basic conditions opens up synthetic routes that would otherwise require tedious protecting-group manipulations. That reputation is not built on sales efforts; it comes straight from project leaders and senior PhDs who measure yield, time, and reproducibility.

    From Glassware to Reactor: Hands-On Process Development

    Producers face a list of real-world constraints, from scalability to sustainability. We invested years in refining our acetylation methods to speed up cleanups and reduce solvent load. The current workflow uses an acylation approach with acetic anhydride and catalytic acid, no magic—just a careful balance between reaction time and temperature. Our operators track exotherms closely, and any deviation flags a supervisor’s attention. Post-reaction workup involves gentle neutralization and multi-step purification: we direct raw output through filters and into rotary evaporators, then dry under reduced pressure.

    Process engineers demand clear data, so every scale-up includes side-by-side analytics: TLC spots, HPLC traces, and NMR spectra confirm reaction completion. Our teams regularly debate whether fractional crystallization or solvent partitioning yields purer product for the next run. These conversations shape batch output every week. On the floor, visible signals often matter more than protocols—slight yellowing or clumping triggers a halt in packing. Chatter in the production area often shifts towards improving crystal size or reducing static. These small points make a difference in how researchers work with the end product, so we pay close attention.

    Quality That Withstands Real-World Shipping and Storage

    Shipping bulk chemicals into global labs brings more trouble than simply sealing a drum and loading a truck. Tri-O-Acetyl-D-Glucal sits among a handful of sugar intermediates that show minor sensitivity to moisture and heat. To protect our shipments, we use multi-layer bags that keep material dry and minimize static buildup during transit. Our packaging team knows which warehouses near ports or airports hold freight longer, so they prioritize double-bagging or extra desiccant inside certain shipments.

    Material arriving at a research facility should look as good on the last day as it did at the plant gate. Over the years, we have taken calls from partners facing product caking or moisture intrusion in regions with high humidity or temperature swings. These experiences led us to design a dual-container system—vacuum-sealed inner bags surrounded by rigid, lined drums. That approach delivers results: repeat partners in tropical and coastal climates stopped reporting spoilage. Our QC team still monitors customer feedback closely, checking returned samples and shipping logs to identify rare problems.

    Comparisons With Similar Carbohydrate Intermediates

    Researchers and formulators regularly swap notes on candidates for sugar-based syntheses. One question recurs: how does Tri-O-Acetyl-D-Glucal compare to other acetylated glucals or related carbohydrate intermediates like methyl glucal or benzyl-protected glucal? The answer depends on experience handling each product at bench or plant scale. Tri-O-Acetyl-D-Glucal stands out because of its robust balance between ease of protection and controlled reactivity. Unlike peracetates, it does not force extra deprotection steps later in a synthetic route. Compared to less-substituted glucals, its three acetyl groups deliver extra stability—less tendency for side reactions or slow hydrolysis under lab conditions.

    Some labs opt for methyl-protected glucals for very sensitive reactions, but that approach often adds extra steps and more aggressive reagents during deprotection. Benzyl-protected forms, while suitable for certain hydrogenation processes, show greater sensitivity to catalytic metals and require specialized waste handling. Through regular customer feedback and our own synthetic testing, the time saved with Tri-O-Acetyl-D-Glucal often outweighs the theoretical advantages of those alternatives. This is especially true for intermediate- to large-scale pharmaceutical manufacturing, where minimizing processing time and material waste drives down cost.

    Usage Practices That Avoid Chasing Repairs

    Working at the source gives our team perspective on what works and what causes frustration in an industrial or research lab. Material integrity drops most often during the measuring and weighing stage. The crystalline powder will clump if left open to humid air. Our best recommendation is to work swiftly and use only the amount required per session, sealing original packaging immediately. For larger preparations, transferring material inside a glovebox or under a dry nitrogen stream offers a reliable solution. We keep silica desiccators on hand across our own labs and recommend the same for any customer storing material over weeks or months rather than days.

    Spills and dust control belong to daily routines. Tri-O-Acetyl-D-Glucal produces minimal airborne dust if handled properly, but static can cause fine particles to adhere to weighing trays. Antistatic brushes and proper grounding of lab benches cut down cleanup time and prevent cross-contamination with other sensitive research chemicals. Our plant safety team regularly discusses spill response with all production staff, ensuring everyone stores containment kits nearby. We encourage similar diligence at customer facilities—not out of compliance, but because we’ve seen the headaches minor lapses create.

    Key Insights for Research and Scale-Up Projects

    Many conversations with partners center on special process requirements: catalyst compatibility, solvent choices, and downstream purification. Tri-O-Acetyl-D-Glucal enters into glycosylation steps as both donor and acceptor, so researchers fine-tune reaction conditions based on supply quality. Common questions involve what works best for cleavage of acetyl groups: most teams find that both mild acid and base catalysis proceed smoothly and predictably on our material, with minimal side products. This has direct consequences for process chemists hunting for scale-up routes with few purification headaches.

    Our technical support fielded more than a few crisis calls over the years—oftentimes from project leaders deep in the middle of challenging syntheses. Working together, we adjust process variables or suggest alternative purification steps. Success in these cases draws directly from hands-on familiarity: we share late-night notes from our own unsuccessful batch runs and hard-won workarounds for removal of stubborn impurities. Some solutions emerge only after repeated trial and error, further underscoring the value of a responsible, experienced production crew engaging directly with researchers.

    Environmental Responsibility Built Into Production

    Manufacturers today face pressure to reduce waste and risk, both to meet regulations and to protect local communities. In our facility, solvent recycling forms a practical cornerstone—acetic acid and organic wash solvents from Tri-O-Acetyl-D-Glucal batches cycle through on-site distillation. We invest in containment and neutralization protocols, catching even trace vented gases via scrubbers. Neighbors and local authorities tour our facility regularly; feedback from those visits shapes our approach more than regulatory bulletins alone.

    A focus on waste minimization extends to packaging steps. We switched from multi-layer plastic overwraps to recyclable, lined paper containers where shipping conditions allow. For consignments headed into harsh climates, our team balances environmental concerns against the real risk of spoiled product—a tightrope made easier by strong relationships with destination labs. This is not just marketing. Every feedback form, every sample return gets logged and reviewed for potential adjustments. Sometimes the best improvements surface in small, seemingly mundane routine checks.

    Supporting Progress in Chemical Research and Production

    Part of our job means following new publications, patent filings, and successful scale-up case studies. Tri-O-Acetyl-D-Glucal continues to appear as a go-to intermediate in emerging synthetic strategies for antiviral, antibacterial, and immunoactive compounds. We have watched teams publish innovative glycosylation protocols relying on its stable, acetyl-protected backbone. Behind these breakthroughs lies a network of supporting suppliers and technical teams dedicated to reliable raw material supply. Our team fields questions not only on product availability, but on process troubleshooting and literature sharing—conversations that build trust as much as finished samples do.

    Having a direct view into what works and what fails pushes us to keep improving each batch. Regular plant meetings bring together process chemists, operators, and QC analysts for open discussions on yields, impurity profiles, and logistics. Improvements in one area often improve results across the board. Our experience with Tri-O-Acetyl-D-Glucal reflects this process: incremental refinements based on practical feedback, not abstract standards.

    Challenges and Shaping Solutions

    No process runs without surprises. Plant operators know to expect occasional bottlenecks in raw material supply, sudden shifts in shipping timelines, or equipment downtime that throws off scheduling. Our crew handles these issues by direct coordination—a phone call to expedite new drums of acetic anhydride, a quick conference to reschedule reactor batches, a backup generator scrambled into use when municipal power drops. In the worst cases, our commitment remains to communicate quickly with partners about affected shipments. Most customers prefer a candid update to last-minute disappointment.

    Scaling production without sacrificing quality brings ongoing debate. We run side-by-side small and large vessel syntheses to observe yield shifts or emerging impurities. No written SOP covers every scenario—that culture of adaptability makes batch-to-batch performance more reliable. We’ve trained a new generation of lab technicians and production workers by sharing these real-world experiences, turning mistakes into stronger processes. Partners relying on Tri-O-Acetyl-D-Glucal tell us these investments show—especially in long-term supply relationships.

    Direct Line Between Manufacturer and User

    Our strongest feedback comes not through formal surveys but from unscripted emails, calls, or lab visit debriefs. Academic teams bring us analytical questions impossible to solve from a distance; commercial partners sometimes ask for custom drying or alternate packaging tailored to local storage conditions. Being both a producer and a sounding board lets us keep pace with evolving needs. Buyers rely on source manufacturers for more than paperwork—they want predictable supply, candid advice, and genuine transparency. That mindset keeps us alert to changing market and research dynamics.

    Tri-O-Acetyl-D-Glucal may never headline a scientific convention, but its importance spreads wherever researchers tackle challenging syntheses involving carbohydrates. Our approach, honed by years of direct chemical production, is grounded in careful observation, hands-on troubleshooting, and open dialogue. Every batch joins a chain of results, discoveries, and improved processes in labs around the world. Being part of that process drives us forward—one run, one feedback loop, one partnership at a time.