61330-62-9

Usage

Uses

Used in Organic Synthesis:
Methyl 2,3,4,6-Tetra-O-benzyl-α-D-mannopyranoside is used as a key intermediate in the synthesis of various complex carbohydrates, glycoconjugates, and other bioactive molecules. Its benzyl-protected structure allows for selective reactions at the free hydroxyl group, enabling the formation of diverse glycosidic linkages and the construction of intricate carbohydrate structures.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Methyl 2,3,4,6-Tetra-O-benzyl-α-D-mannopyranoside is utilized as a building block for the synthesis of glycoproteins, glycolipids, and other carbohydrate-based drugs. These glycoconjugates play crucial roles in various biological processes, such as cell recognition, immune response, and cell signaling. Methyl 2,3,4,6-Tetra-O-benzyl-a-D-mannopyranoside's ability to form specific glycosidic linkages contributes to the development of novel therapeutic agents with improved efficacy and selectivity.
Used in Chemical Research:
Methyl 2,3,4,6-Tetra-O-benzyl-α-D-mannopyranoside is also employed as a research tool in the field of carbohydrate chemistry. It serves as a model compound for studying the reactivity and selectivity of various glycosylation reactions, as well as the development of new synthetic methods and catalysts for carbohydrate synthesis. This research contributes to a better understanding of carbohydrate structure and function, and the discovery of new carbohydrate-based drugs and materials.
Used in Material Science:
In material science, Methyl 2,3,4,6-Tetra-O-benzyl-α-D-mannopyranoside can be used as a building block for the synthesis of carbohydrate-based polymers and materials. These materials have potential applications in various fields, such as drug delivery, tissue engineering, and biocompatible coatings, due to their unique properties, such as biocompatibility, biodegradability, and specific interactions with biological systems.

InChI:InChI=1/C35H38O6/c1-36-35-34(40-25-30-20-12-5-13-21-30)33(39-24-29-18-10-4-11-19-29)32(38-23-28-16-8-3-9-17-28)31(41-35)26-37-22-27-14-6-2-7-15-27/h2-21,31-35H,22-26H2,1H3/t31?,32-,33+,34-,35+/m1/s1

Upstream product

• 67-56-1 methanol 
• 38184-10-0 phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 6564-72-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 129470-73-1 S-1-(1'-phenyl-1H-tetrazolyl) 2,3,4,6-tetra-O-benzyl-β-D-glucopyranose 
• 78153-79-4 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl fluoride 
• 89025-46-7 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl fluoride 
• 126709-14-6 1-Azi-2,3,4,6-tetra-O-benzyl-1-deoxy-D-glucopyranose 
• 74352-41-3 2-Pyridyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside 
• 144490-57-3 2-pyridyl 2,3,4,6-tetra-O-benzyl-1-thio-αβ-D-glucopyranoside 
• 19488-61-0 methyl 2,3,4,6-tetra-O-benzyl α-D-glucopyranoside 
• 681-84-5 tetramethylorthosilicate 
• 1825-61-2 Trimethylmethoxysilane 
• 100-39-0 benzyl bromide 

Downstream Products

• 91510-87-1 2-methyl-3-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)propene 
• 91510-87-1 2-methyl-3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)propene 
• 92413-81-5 3-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)butene 
• 92413-82-6 2-bromo-3-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)propene 
• 91602-61-8 phenyl 2,3,4,6-tetra-O-benzyl-1-thio-α/β-D-glucopyranoside 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 56822-49-2 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranoside 
• 82231-38-7 methyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 81972-19-2 1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-2-propene 
• 82659-52-7 1-(2,3,4,6-O-tetrabenzyl-α-D-glucopyranosyl)-2-propene 
• 6564-72-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 59531-24-7 2,3,4,6-tetra-O-benzyl-D-glucopyranoside 
• 4356-77-8 acetyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranoside 

Relevant academic research and scientific papers

Discovery of Salidroside-Derivated Glycoside Analogues as Novel Angiogenesis Agents to Treat Diabetic Hind Limb Ischemia

Therapeutic angiogenesis is a potential therapeutic strategy for hind limb ischemia (HLI); however, currently, there are no small-molecule drugs capable of inducing it at the clinical level. Activating the hypoxia-inducible factor-1 (HIF-1) pathway in skeletal muscle induces the secretion of angiogenic factors and thus is an attractive therapeutic angiogenesis strategy. Using salidroside, a natural glycosidic compound as a lead, we performed a structure-activity relationship (SAR) study for developing a more effective and druggable angiogenesis agent. We found a novel glycoside scaffold compound (C-30) with better efficacy than salidroside in enhancing the accumulation of the HIF-1α protein and stimulating the paracrine functions of skeletal muscle cells. This in turn significantly increased the angiogenic potential of vascular endothelial and smooth muscle cells and, subsequently, induced the formation of mature, functional blood vessels in diabetic and nondiabetic HLI mice. Together, this study offers a novel, promising small-molecule-based therapeutic strategy for treating HLI.

Streamlined access to carbohydrate building blocks: Methyl 2,4,6-tri-O-benzyl-α-D-glucopyranoside

Presented herein is an improved synthesis of a common 3-OH glycosyl acceptor. This compound is a building block that is routinely synthesized by many research groups to be used in glycosylation refinement studies. The only known direct synthesis by Koto lacks regioselectivity and relies on chromatography separation using hazardous solvents. Our improved synthetic approach relies on Koto's selective benzylation protocol, but it is followed by acylation-purification-deacylation sequence. Although this approach involves additional manipulations, it provides consistent results and is superior to other indirect strategies. Also obtained, albeit in minor quantities, is 4-OH acceptor, another common building block.

Automated Quantification of Hydroxyl Reactivities: Prediction of Glycosylation Reactions

The stereoselectivity and yield in glycosylation reactions are paramount but unpredictable. We have developed a database of acceptor nucleophilic constants (Aka) to quantify the nucleophilicity of hydroxyl groups in glycosylation influenced by the steric, electronic and structural effects, providing a connection between experiments and computer algorithms. The subtle reactivity differences among the hydroxyl groups on various carbohydrate molecules can be defined by Aka, which is easily accessible by a simple and convenient automation system to assure high reproducibility and accuracy. A diverse range of glycosylation donors and acceptors with well-defined reactivity and promoters were organized and processed by the designed software program “GlycoComputer” for prediction of glycosylation reactions without involving sophisticated computational processing. The importance of Aka was further verified by random forest algorithm, and the applicability was tested by the synthesis of a Lewis A skeleton to show that the stereoselectivity and yield can be accurately estimated.

Tuning the activity of iminosugars: novel N-alkylated deoxynojirimycin derivatives as strong BuChE inhibitors

We have designed unprecedented cholinesterase inhibitors based on 1-deoxynojirimycin as potential anti-Alzheimer’s agents. Compounds are comprised of three key structural motifs: the iminosugar, for interaction with cholinesterase catalytic anionic site (

Highly regioselective and stereoselective synthesis of C-Aryl glycosidesvianickel-catalyzedortho-C-H glycosylation of 8-aminoquinoline benzamides

C-Aryl glycosides are of high value as drug candidates. Here a novel and cost-effective nickel catalyzedortho-CAr-H glycosylation reaction with high regioselectivity and excellent α-selectivity is described. This method shows great functional group compatibility with various glycosides, showing its synthetic potential. Mechanistic studies indicate that C-H activation could be the rate-determining step.

Design, synthesis, and biological evaluation of desmuramyl dipeptides modified by adamantyl-1,2,3-triazole

Muramyl dipeptide (MDP) is the smallest peptidoglycan fragment able to trigger the immune response. Structural modification of MDP can lead to the preparation of analogs with improved immunostimulant properties, including desmuramyl peptides (DMPs). The aim of this work was to prepare the desmuramyl peptide (L-Ala-D-Glu)-containing adamantyl-triazole moiety and its mannosylated derivative in order to study their immunomodulatory activities in vivo. The adjuvant activity of the prepared compounds was evaluated in a murine model using ovalbumin as an antigen, and compared to the reference adjuvant ManAdDMP. The results showed that the introduction of the lipophilic adamantyl-triazole moiety at the C-terminus of L-Ala-D-Glu contributes to the immunostimulant activity of DMP, and that mannosylation of DMP modified with adamantyl-triazole causes the amplification of its immunostimulant activity.

Glucosylpolyphenols as Inhibitors of Aβ-Induced Fyn Kinase Activation and Tau Phosphorylation: Synthesis, Membrane Permeability, and Exploratory Target Assessment within the Scope of Type 2 Diabetes and Alzheimer's Disease

Despite the rapidly increasing number of patients suffering from type 2 diabetes, Alzheimer's disease, and diabetes-induced dementia, there are no disease-modifying therapies that are able to prevent or block disease progress. In this work, we investigate the potential of nature-inspired glucosylpolyphenols against relevant targets, including islet amyloid polypeptide, glucosidases, and cholinesterases. Moreover, with the premise of Fyn kinase as a paradigm-shifting target in Alzheimer's drug discovery, we explore glucosylpolyphenols as blockers of Aβ-induced Fyn kinase activation while looking into downstream effects leading to Tau hyperphosphorylation. Several compounds inhibit Aβ-induced Fyn kinase activation and decrease pTau levels at 10 μM concentration, particularly the per-O-methylated glucosylacetophloroglucinol and the 4-glucosylcatechol dibenzoate, the latter inhibiting also butyrylcholinesterase and β-glucosidase. Both compounds are nontoxic with ideal pharmacokinetic properties for further development. This work ultimately highlights the multitarget nature, fine structural tuning capacity, and valuable therapeutic significance of glucosylpolyphenols in the context of these metabolic and neurodegenerative disorders.

C-MANNOSIDE COMPOUNDS USEFUL FOR THE TREATMENT OF URINARY TRACT INFECTIONS

Disclosed herein are new C-mannoside compounds and compositions and their application as pharmaceuticals for the treatment of human disease. Methods of inhibition of FimH activity in a human subject are also provided for the treatment diseases such as urinary tract infection.

C-Mannosyl Lysine for Solid Phase Assembly of Mannosylated Peptide Conjugate Cancer Vaccines

Dendritic cells (DCs) are armed with a multitude of Pattern Recognition Receptors (PRRs) to recognize pathogens and initiate pathogen-tailored T cell responses. In these responses, the maturation of DCs is key, as well as the production of cytokines that help to accomplish T cell responses. DC-SIGN is a frequently exploited PRR that can effectively be targeted with mannosylated antigens to enhance the induction of antigen-specific T cells. The natural O-mannosidic linkage is susceptible to enzymatic degradation, and its chemical sensitivity complicates the synthesis of mannosylated antigens. For this reason, (oligo)mannosides are generally introduced in a late stage of the antigen synthesis, requiring orthogonal conjugation handles for their attachment. To increase the stability of the mannosides and streamline the synthesis of mannosylated peptide antigens, we here describe the development of an acid-stable C-mannosyl lysine, which allows for the inline introduction of mannosides during solid-phase peptide synthesis (SPPS). The developed amino acid has been successfully used for the assembly of both small ligands and peptide antigen conjugates comprising an epitope of the gp100 melanoma-associated antigen and a TLR7 agonist for DC activation. The ligands showed similar internalization capacities and binding affinities as the O-mannosyl analogs. Moreover, the antigen conjugates were capable of inducing maturation, stimulating the secretion of pro-inflammatory cytokines, and providing enhanced gp100 presentation to CD8+ and CD4+ T cells, similar to their O-mannosyl counterparts. Our results demonstrate that the C-mannose lysine is a valuable building block for the generation of anticancer peptide-conjugate vaccine modalities.

Mapping mechanisms in glycosylation reactions with donor reactivity: Avoiding generation of side products

The glycosylation reaction, which is key for the studies on glycoscience, is challenging due to its complexity and intrinsic side reactions. Thioglycoside is one of the most widely used glycosyl donors in the synthesis of complex oligosaccharides. However, one of the challenges is its side reactions, which lower its yield and limits its efficiency, thereby requiring considerable effort in the optimization process. Herein, we reported a multifaceted experimental approach that reveals the behaviors of side reactions, such as the intermolecular thioaglycon transformation and N-glycosyl succinimides, via the glycosyl intermediate. Our mechanistic proposal was supported by low temperature NMR studies that can further be mapped by utilizing relative reactivity values. Accordingly, we also presented our findings to suppress the generation of side products in solving this particular problem for achieving high-yield glycosylation reactions.