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2-Acetamido-2-Deoxy-Alpha-D-Glucopyranosyl Chloride 3,4,6-Triacetate

    • Product Name 2-Acetamido-2-Deoxy-Alpha-D-Glucopyranosyl Chloride 3,4,6-Triacetate
    • Alias GlcNAc-Cl
    • Einecs 629-622-9
    • 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

    261901

    Cas Number 7517-07-3
    Molecular Formula C16H22ClNO9
    Molecular Weight 407.80
    Iupac Name (2R,3R,4R,5S,6R)-2-(Acetylamino)-3,4,6-triacetoxy-2-deoxy-α-D-glucopyranosyl chloride
    Appearance White to off-white powder
    Solubility Soluble in chloroform, dichloromethane; sparingly soluble in water
    Melting Point 172-175°C
    Storage Temperature Store at 2-8°C
    Synonyms Glucosamine chloride triacetate, 3,4,6-Tri-O-acetyl-2-acetamido-2-deoxy-α-D-glucopyranosyl chloride
    Purity Typically >98%
    Boiling Point Decomposes before boiling
    Smiles CC(=O)N[C@@H]1O[C@H](O[C@H]([C@@H]([C@H]1Cl)OC(=O)C)OC(=O)C)COC(=O)C

    As an accredited 2-Acetamido-2-Deoxy-Alpha-D-Glucopyranosyl Chloride 3,4,6-Triacetate factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.

    Packing & Storage
    Packing Amber glass vial containing 1 gram of 2-Acetamido-2-Deoxy-Alpha-D-Glucopyranosyl Chloride 3,4,6-Triacetate, sealed under inert atmosphere.
    Shipping The chemical **2-Acetamido-2-Deoxy-Alpha-D-Glucopyranosyl Chloride 3,4,6-Triacetate** is shipped in sealed, inert containers under dry and cool conditions. Packaging complies with all regulatory standards for hazardous chemicals, ensuring protection from moisture and air. Transport is via certified chemical carriers, with appropriate labeling and documentation for safe, compliant handling and delivery.
    Storage Store **2-Acetamido-2-Deoxy-Alpha-D-Glucopyranosyl Chloride 3,4,6-Triacetate** in a tightly sealed container under an inert atmosphere, such as nitrogen or argon, in a cool, dry place away from moisture and direct sunlight. Keep at 2–8°C (refrigerator) and protect from strong acids, bases, and oxidizing agents. Handle only in a well-ventilated area using proper personal protective equipment.
    Application of 2-Acetamido-2-Deoxy-Alpha-D-Glucopyranosyl Chloride 3,4,6-Triacetate

    Applications of 2-Acetamido-2-Deoxy-Alpha-D-Glucopyranosyl Chloride 3,4,6-Triacetate in Industrial Manufacturing

    As a manufacturer specializing in carbohydrate chemistry, we supply 2-Acetamido-2-Deoxy-Alpha-D-Glucopyranosyl Chloride 3,4,6-Triacetate as a key intermediate for advanced glycosylation processes in several demanding industrial sectors. This page details established, large-scale application scenarios where our material supports downstream integration within controlled standards, specified dosages, and precise manufacturing protocols.

    1. Active Pharmaceutical Ingredient (API) Synthesis for Glycosylated Drugs

    Pharmaceutical manufacturers incorporate our raw material as a protected glycosyl donor during the synthesis of N-acetylglucosamine-containing APIs, including glycopeptide antibiotics and select antiviral compounds. Specialized protection profiles allow for selective deprotection and glycosylation steps under controlled conditions. API synthesis plants utilize this intermediate at the convergent glycosylation stage, ensuring traceable handling and batch reproducibility for clinical API production.

    Industry compliance standards

    • ICH Q7 Good Manufacturing Practices for Active Pharmaceutical Ingredients
    • USP-NF and European Pharmacopoeia monographs where applicable
    • FDA 21 CFR Part 210/211 for finished pharmaceuticals
    • EDQM GMP guidelines for advanced intermediates

    Typical usage ratio

    • 0.7–1.0 molar equivalents per targeted glycosylation site; typically optimized by process chemists relative to acceptor in multi-step reactions

    Downstream process integration

    • Introduced during protective group chemistry for downstream glycosyl donor preparation
    • Enters automated reactor systems in solution phase, under inert gas and controlled temperature (0°C to ambient)
    • Feeds directly into glycosylation reactors, followed by selective deprotection and coupling with aglycone or peptide acceptors

    Final product types

    • Glycosylated peptide antibiotics (e.g., vancomycin derivatives)
    • Sugar-modified antiviral nucleosides
    • N-acetylglucosamine-based pharmaceutical APIs

    2. Oligosaccharide Synthesis for Therapeutic Glycans

    Manufacturers of oligosaccharide libraries and therapeutic glycans rely on this protected monosaccharide chloride as an efficient glycosyl donor for controlled construction of branched and linear GlcNAc-rich oligosaccharides. Reproducible introduction of N-acetylglucosamine moieties in a multi-step process enables delivery of defined glycan structures, which are in demand for preclinical and clinical research, as well as biopharmaceutical glycoengineering.

    Industry compliance standards

    • ISO 9001:2015 Quality Management System
    • Custom product release criteria aligned with analytical documentation (HPLC, NMR, MS)
    • GLP and cGMP guidelines for preclinical glycan manufacturing
    • OECD Good Laboratory Practice for analytical traceability

    Typical usage ratio

    • 1.0–1.3 eq. per glycosylation step, depending on acceptor group reactivity and targeted oligosaccharide chain length

    Downstream process integration

    • Dissolved into dry organic solvent (<1% moisture) for precise coupling under Lewis acid catalysis
    • Implemented during iterative glycosylation cycles on automated carbohydrate synthesizers
    • Automated workup for by-product removal with intermediary purification via column chromatography

    Final product types

    • Defined GlcNAc-oligosaccharide reference standards
    • Synthetic therapeutic glycans for immunotherapy studies
    • Glycoconjugate building blocks for vaccine research

    3. Glycopolymer and Functional Polymer Modification

    Producers of specialty polymers employ this intermediate during post-polymerization functionalization, especially for introducing pendant N-acetylglucosamine residues onto polymer backbones. The selective reactivity of the protected glycosyl chloride facilitates grafting onto activated polymer sites, imparting bioactivity, increased hydrophilicity, or anti-biofouling characteristics relevant for biomedical and diagnostic devices.

    Industry compliance standards

    • REACH Regulation (EC) No 1907/2006 for chemical safety
    • ISO 10993-5 for polymer biocompatibility (as required for medical device contact layers)
    • QMS aligned with ISO 13485 where polymer applications involve regulated medical devices

    Typical usage ratio

    • 5–15% w/w relative to polymer mass, based on intended density of GlcNAc units and application requirements

    Downstream process integration

    • Added post-polymerization in solution with in-situ activation of pendant functional groups (e.g., amines or alcohols)
    • Reaction performed in anhydrous conditions at 20–60°C to avoid hydrolysis
    • Followed by deprotection steps to yield free GlcNAc functional groups on the polymer

    Final product types

    • Biofunctional films for cell culture scaffolds
    • Glycosylated coatings for microfluidic chips
    • Hydrogel substrates with anti-fouling properties

    4. Diagnostic Reagent Synthesis for Glycoanalysis

    Key manufacturers in the IVD and research reagent industries use this compound to prepare specific chromogenic or fluorescent glycosides for enzymatic glycoanalysis kits. High purity and reactivity allow for selective attachment of reporter groups to N-acetylglucosamine, enabling sensitive substrate preparation for quantification of glycosidase activities in complex biological samples.

    Industry compliance standards

    • ISO 13485:2016 for medical device reagent manufacturing
    • EU IVDD 98/79/EC for in vitro diagnostic reagents (or IVDR for recent product registrations)
    • Good Laboratory Practice (GLP) for batch records and analytical validation

    Typical usage ratio

    • 1.0 equivalent with respect to chromogenic/fluorogenic acceptor groups; exact ratio varies per substrate synthesis protocol

    Downstream process integration

    • Used as primary glycosyl donor in the conjugation step with chromophores or enzymatic labels
    • Fed into stirred reaction vessels under dry conditions and monitored by TLC/HPLC for completion
    • Purified by preparative chromatography before quality control release

    Final product types

    • pNP-GlcNAc and similar chromogenic glycoside substrates
    • Fluorogenic GlcNAc derivatives for glycosidase detection assays
    • Biotinylated glycan probes for scientific kits
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    Certification & Compliance
    More Introduction

    Introducing 2-Acetamido-2-Deoxy-Alpha-D-Glucopyranosyl Chloride 3,4,6-Triacetate: Genuine Manufacturer Perspective

    Shaping Precision in Modern Carbohydrate Chemistry

    We have worked with 2-Acetamido-2-Deoxy-Alpha-D-Glucopyranosyl Chloride 3,4,6-Triacetate for years on the production floor, overseeing raw material selection, synthesizing batches under meticulously controlled conditions, and handling every drum coming off the line. This compound, often simply called Triacetate Glucosaminyl Chloride, draws demand from labs and multistage synthesis shops for its critical role as a glycosyl donor. The expertise required to keep the product consistently high-purity and stable over months speaks to the challenges of producing fine carbohydrate building blocks at scale — and explains why customers demand experienced, fully traceable manufacturing practices.

    Clear Specifications Define Real-World Usability

    What does this product bring to the bench? The chemical comes as a white or very pale crystalline powder, with a molecular formula of C14H20ClNO8 and a molecular weight of 381.76 g/mol. Lab teams want to see a product with high purity, usually over 98%, as even minor impurities interfere in glycosylation reactions. During our own QC, we’ve seen firsthand that residues under 2% — such as unprotected hydroxy groups or unconverted starting materials — can ruin batch yields for advanced oligosaccharide synthesis. Testing never takes a back seat; we apply HPLC, NMR, and sometimes mass spectrometry to confirm the product’s structure and ensure batch-to-batch reproducibility. No ambiguous color or mystery odor: every lot leaves our warehouse meeting tight standards, verified by a crew who knows both carbohydrate chemistry and the pain caused by corners cut upstream.

    Manufacturing Experience: Building Trust Through Reproducibility

    People often overlook the scale-up headaches with glycosyl donors like this one. We’ve been down the path of adjusting reaction parameters for exothermic acetylations, purifying across columns over and over to chase out persistent yellow residues, and balancing moisture control throughout storage and packaging. In our plant, process engineers stand at the reactor, not just behind a desk. Raw glucosamine hydrochloride must undergo acetylation and chlorination under anhydrous conditions, followed by purification that leaves no persistent acid traces. Vacuum-drying and double-bagging in an inert atmosphere guard against hydrolysis and caking in warm weather. Our teams keep detailed batch records, cross-check every kilogram, and commit to full re-testing before international shipments.

    Why Product Consistency Matters

    Synthetic carbohydrate chemistry puts huge pressure on every gram of donor and acceptor. For glycosylation strategies that leverage this triacetate-protected glucosaminyl chloride, the compound must be ready for rapid, high-yield coupling. Researchers and pharma API project managers have shown that even slightly degraded or over-aged batches can kill yields or complicate purification downstream. Moisture control is a recurrent concern; once we battled through a humid season only to spot subtle hydrolysis at final QC, teaching us the value of robust drying procedures and sealed, moisture-impermeable containers. These lessons don’t come from theory — the experience of cleaning up and reworking a failed drum gives weight to every improvement in packing and logistics.

    What Sets 2-Acetamido-2-Deoxy-Alpha-D-Glucopyranosyl Chloride 3,4,6-Triacetate Apart?

    The market offers several glycosyl donors, yet this compound serves as a key intermediate for synthesizing N-acetylglucosamine-containing oligosaccharides and related glycoconjugates. Unlike peracetylated donors lacking the key N-acetyl group, this molecule offers chemoselective access to biologically relevant glycan motifs. In the hands of carbohydrate chemists, it becomes a powerful reagent for building glycosidic bonds under Koenigs-Knorr and other activation methods. Compared to bromide analogues — which may offer greater reactivity — the chloride brings improved stability, better control at ambient conditions, and typically cleaner conversion in controlled glycosylation environments. Our regular customers, working on vaccine adjuvant APIs or targeting glycopeptide constructs, rely on these distinctions to bridge the gap between academic-scale successes and production runs for clinical supply.

    Product Use: From Research Bench to Pilot Plant

    Every batch receives its main test on an actual synthesis. Researchers find that this compound dissolves well in anhydrous dichloromethane, methanol, or similar solvents. The glycosyl chloride group reacts smoothly with glycosyl acceptors containing free hydroxyl groups, aided by silver salts or other activating agents. These reactions run at controlled temperatures, often between -30°C and room temperature, to avoid side reactions or racemization. The acetyl groups serve to protect sensitive alcohol groups during the coupling step, crucial for complex, multi-step oligosaccharide synthesis.

    From a manufacturer’s lens, handling practices also shape the end-user’s experience. Operators must avoid exposure to even minimal humidity, since glycosyl chlorides are known to hydrolyze, forming glycosyl hemiacetals and losing activating ability. We continue to improve our isolation and packaging protocols so every user — whether in academia or industry — gets a powder that mirrors freshly produced product, not a degraded or heterogeneous blend. Beyond synthesis, fully protected derivatives like this one allow for storage under refrigeration without concern for rapid decomposition, offering more flexibility for project timing.

    Differences from Other Protected Glycosyl Chlorides

    Triacetate-protected glucosaminyl chlorides differ significantly from their peracetylated or perbenzoylated cousins. The main distinction comes from the specific N-acetyl functionality at the C-2 position; this moiety matches the structure found in important biological glycans such as chitin, glycosaminoglycans, and O-GlcNAc modified proteins. Unlike totally acetylated hexosyl chlorides, the 2-acetamido group blocks competitive reactions and imparts unique chemical stability. For end-users wishing to assemble bioactive glycans or prepare N-acetylglucosamine repeating units, this exact pattern of protection and activation is vital.

    Other glycosyl chlorides available in the market may offer per-acetyl protection across all hydroxyls but lack the distinctive amide at C-2. Those products usually serve for general hexose backbone assembly, not for critical biomedical targets or recombinant glycoprotein analogues. In our own experience, neglecting this key group during the design of a synthesis often means wasted runs and poor final product authenticity. Purity also sets this version apart. Unreacted starting material, residual acids, or acetyl migration byproducts, observed in poorly controlled syntheses, make downstream reactions erratic. We monitor for these issues during every batch, learning from years of repeated analysis and feedback from users who outline precisely how batch-to-batch variation disrupts their project flow. In the end, our attention to these details saves valuable research time for our customers.

    Applications: Real-Life Demands and Solutions

    Our largest customers—ranging from national biotech institutes to small specialty pharma groups—frequently ask about scalability and handling reliability. Triacetate-protected glucosaminyl chlorides play a role in synthesizing defined glycopeptide antigens for vaccine R&D, as well as in advanced carbohydrate conjugates for drug-discovery platforms. Several clients have pushed us for larger batch sizes and longer stability claims, requiring us to adapt production and review rigorous accelerated aging data. By storing the product at controlled low temperatures, with fully dry and oxygen-free packaging, we consistently deliver product that meets both the academic and pilot plant requirements for multi-gram synthesis.

    This compound also appears in studies focused on bacterial cell wall analogues, heparin mimetics, and O-linked glycan probes. Here, the precise protection pattern of the molecule lets researchers install N-acetylglucosamine at the correct glycosidic linkage, tracking cell signaling or building synthetic antigens. More than once, feedback from pioneering labs has prompted us to expand our analytical toolkit and fine-tune impurity thresholds, reflecting the fact that published research and patent filings depend on well-characterized and homogenous inputs. Concerns about storage and long-distance shipping—especially faced by international institutions—have honed our ongoing improvements in both product stability and document support.

    From Bulk Production to the World’s Laboratories

    What distinguishes direct manufacturers from resellers lies in the visible hands-on experience. Our technical team not only manages day-to-day synthesis and QC, but also troubleshoots packaging failures and learns from every domestic or international shipment. Moisture ingress, inadvertent light exposure, or accidental temperature abuse remain persistent headaches for buyers working at a distance—but solving these problems upstream, before the drum is crated, cuts down on lost material and frustrated project timelines.

    We have also fielded specific requests, such as producing the compound to custom particle-size ranges or making sure certain potentially reactive side products are removed to sub-0.1% levels. Responding quickly comes easier when teams are trained on the full arc of production and aware of the downstream chemistry. As other manufacturers have sometimes learned the hard way, the true discipline of carbohydrate synthesis demands batches that perform consistently in highly sensitive coupling reactions—not just on paper, but in the hands of scientists trying to build the next generation of therapeutics and analytical tools.

    End-User Recommendations Drawn from Hands-On Practice

    Carbohydrate chemistry rewards attention to detail and punishes shortcuts. Proper handling starts with storing the product at or below -20°C in moisture-proof, light-blocking containers. Scoops and weighing tools should be fully dry, and containers closed promptly after sampling. Chemists should dissolve the compound in rigorously dried solvents in a glovebox or under inert gas when targeting best yields. Activation methods differ: we have seen teams reliably use silver triflate or silver carbonate, among other promotors, prompted by published procedures and our own direct support experience.

    Deprotection of the acetyl groups proceeds with standard mild base hydrolysis or enzymatic approaches, depending on project needs. Many users successfully transition from bench-modest glycosylations to larger parallel runs, provided the starting chloride remains free of decomposition and trace acids. Our customer support group stays in regular contact with users needing tips on work-up, showing that even academically published procedures often require tweaks when going upscale or handling gram-to-kg quantities.

    Continuous Improvement Driven by Client Partnerships

    Since entering the production field, we have partnered with technical specialists across pharmaceutical, biotech, and chemical research communities. Receiving direct feedback about side reactions, storage quirks, or batch-to-batch performance challenges enables ongoing review and incremental process refinements. Real-world usage examples drive our innovation—a customer working on an oligosaccharide vaccine experienced difficulty in downstream purification until minor aldehyde impurities were purged from the process. Following this, we introduced extra purification steps and adjusted our moisture targets, improving outcomes for every subsequent user.

    A commitment to learning goes hand in hand with regulatory and documentation responsibilities. We maintain transparent batch records, offer comprehensive analytical data, and respond to customer inquiries with site-specific knowledge. Refinements in our technical documentation were prompted by a client’s question on batch re-testing intervals, prompting us to expand our shelf-life study framework and support robust project timelines. This ongoing relationship means our users trust not just the quality at delivery, but also traceability and backup samples for regulatory or reproducibility checks.

    Meeting the Future Needs of Saccharide Chemistry

    Research, regulatory, and application demands keep rising. With advanced glycoscience moving into areas such as site-specific biologic modification, clean-room production of glycan-based diagnostics, and synthesis of immunogenic carbohydrate epitopes, the quality and availability of specialized protected glycosyl chlorides have never been more crucial. We prepare for this by keeping our plant current, our team trained, and our analytical facilities ready for new challenges — ensuring each batch supports the increasingly sophisticated requirements of carbohydrate researchers worldwide.

    Our journey with 2-Acetamido-2-Deoxy-Alpha-D-Glucopyranosyl Chloride 3,4,6-Triacetate brings together hard-won experience, chemist-to-chemist collaboration, and a relentless push for improvement. From first-time customers exploring protected glucosaminyl chemistry to established partners preparing clinical supply materials, our team puts real-world experience and scientific rigor at the heart of every batch. This is how we continue to contribute to the global advance of carbohydrate science—by providing quality, consistency, and honest insight, grown from hands-on manufacturing know-how.