4148-58-7

Usage

Uses

Used in Pharmaceutical Industry:
METHYL 4,6-O-BENZYLIDENE-A-D-MANNOPYRANOSIDE is used as an active pharmaceutical ingredient for its in vitro antibacterial activity. It demonstrates potential in the development of new antibiotics to combat bacterial infections.
Used in Chemical Research:
As a white to off-white solid, METHYL 4,6-O-BENZYLIDENE-A-D-MANNOPYRANOSIDE can be utilized in chemical research for the synthesis of various derivatives and compounds, contributing to the advancement of chemical science and technology.
Used in Material Science:
The unique chemical properties of METHYL 4,6-O-BENZYLIDENE-A-D-MANNOPYRANOSIDE may also find applications in material science, where it could be used to develop new materials with specific properties, such as improved strength, durability, or biocompatibility.

Upstream product

• 1125-88-8 benzaldehyde dimethyl acetal 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 100-52-7 benzaldehyde 
• 2774-22-3 2,3-O-diacetyl-(4,6-O-benzylidene)methyl-α-D-mannopyranoside 
• 65530-27-0 (2R,4aR,6S,8aS)-(+)-6-methoxy-2-phenyl-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxine 
• 618-31-5 benzylidene dibromide 
• 73395-15-0 methyl endo(phenyl)-2,3:4,6-di-O-benzylidene-α-D-mannopyranoside 
• 91685-06-2 methyl 2-O-benzoyl-4, 6-O-benzylidene-α-D-mannopyranoside 
• 774-48-1 (diethoxymethyl)benzene 
• 1824-94-8 methyl beta-D-galactopyranoside 
• 82430-07-7 (4S,5R)-5-((R)-1-Methoxy-2-oxo-ethoxy)-2-phenyl-[1,3]dioxane-4-carbaldehyde 
• 3162-96-7 methyl 4,6-O-benzylidene-β-D-galactopyranoside 
• 4148-71-4 (2S,3aS,4S,5aR,9aR,9bS)-4-Methoxy-2,8-diphenyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxine 
• 530-26-7 D-Mannose 

Downstream Products

• 74984-87-5 Methyl-4,5-O-benzyliden-2,3-carbonato-α-D-mannopyranosid 
• 120200-50-2 methyl 4,6-O-benzylidene-2,3-di-O-methyl-α-D-mannopyranoside 
• 7177-79-9 methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside 
• 151526-84-0 methyl 4,6-O-benzylidene-α-D-galactopyranoside 2,3-bis(methanesulfonate) 
• 186539-95-7 methyl 4,6-O-benzylidene-3-O-ethyl-α-D-mannopyranoside 
• 65877-24-9 methyl 3-O-allyl-4,6-O-benzylidene-α-D-mannopyranoside 
• 216758-62-2 methyl-4,6-O-benzylidene-3-O-(p-methoxybenzyl)-α-D-mannopyranoside 
• 288104-42-7 Phthalic acid 1-((2R,4aR,6S,7S,8S,8aS)-8-hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl) ester 2-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl) ester 
• 74984-85-3 methyl-4,6-O-phenylmethylene-2,3-thionocarbonyl-α-D-mannopyranoside 
• 293728-88-8 methyl-4,6-O-phenylmethylene-3-O-phenylthionocarbonyl-α-D-mannopyranoside 
• 431981-81-6 methyl 3-O-allyl-2,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->3)-4,6-O-benzylidene-α-D-mannopyranoside 
• 440339-63-9 methyl 2,3-di-O-benzoyl-5,6-O-isopropylidene-β-D-galactofuranosyl-(1->3)-4,6-O-benzylidene-α-D-mannopyranoside 

Relevant academic research and scientific papers

General Strategy for the Synthesis of Rare Sugars via Ru(II)-Catalyzed and Boron-Mediated Selective Epimerization of 1,2- trans-Diols to 1,2- cis-Diols

Human glycans are primarily composed of nine common sugar building blocks. On the other hand, several hundred monosaccharides have been discovered in bacteria and most of them are not readily available. The ability to access these rare sugars and the corresponding glycoconjugates can facilitate the studies of various fundamentally important biological processes in bacteria, including interactions between microbiota and the human host. Many rare sugars also exist in a variety of natural products and pharmaceutical reagents with significant biological activities. Although several methods have been developed for the synthesis of rare monosaccharides, most of them involve lengthy steps. Herein, we report an efficient and general strategy that can provide access to rare sugars from commercially available common monosaccharides via a one-step Ru(II)-catalyzed and boron-mediated selective epimerization of 1,2-trans-diols to 1,2-cis-diols. The formation of boronate esters drives the equilibrium toward 1,2-cis-diol products, which can be immediately used for further selective functionalization and glycosylation. The utility of this strategy was demonstrated by the efficient construction of glycoside skeletons in natural products or bioactive compounds.

Acceleration and deceleration factors on the hydrolysis reaction of 4,6-O-benzylidene acetal group

The benzylidene acetal group is one of the most important protecting groups not only in carbohydrate chemistry but also in general organic chemistry. In the case of 4,6-O-benzylidene glycosides, we previously found that the stereochemistry at 4-position altered the reaction rate constant for hydrolysis of benzylidene acetal group. However, a detail of the acceleration or deceleration factor was still unclear. In this work, the hydrolysis reaction of benzylidene acetal group was analyzed using the Arrhenius and Eyring plot to obtain individual parameters for glucosides (Glc), mannosides (Man), and galactosides (Gal). The Arrhenius and Eyring plot indicated that the pre-exponential factor (A) and ΔS? were critical for the smallest reaction rate constant of Gal among nonacetylated substrates. On the other hand, both Ea/ΔH? and A/ΔS? were influential for the smallest reaction rate constant of Gal among diacetylated substrates. All parameters obtained suggested that the rate constant for hydrolysis reaction was regulated by protonation and hydration steps along with solvation. The obtained parameters support wide use of benzylidene acetal group as orthogonal protection of cis- and trans-fused bicyclic systems through the fast hydrolysis of the trans-fused benzylidene acetal group.

Exploration of the Fluoride Reactivity of Aryltrifluoroborate on Selective Cleavage of Diphenylmethylsilyl Groups

The first known report on the fluoride catalytic reactivity of potassium aryltrifluoroborate is described. The fluoride reactivity of phenyltrifluoroborate was controlled by substituents on the trifluoroborate-attached benzene, such as the methoxy group a

One-pot synthesis of orthogonally protected sugars through sequential base-promoted/acid-catalyzed steps: A solvent-free approach with self-generation of a catalytic species

A varied set of solvent-free, one-pot synthetic sequences were developed to carry out the orthogonal protection of saccharide polyols. These sequences are composed of an initial regioselective benzylation, silylation or iodination (under mildly basic cond

Conformational analysis of the disaccharide methyl a-d-mannopyranosyl-(1→3)-2-O-acetyl-β-D-manno-pyranoside monohydrate

The crystal structure of methyl β-d-mannopyranosyl-(1→3)-2-O-acetyl-β-d-mannopyranoside monohydrate, C15H26O12.H2O, (II), has been determined and the structural parameters for its constituent β-d-mannopyranosyl residue compared with those for methyl β-d-mannopyranoside. Mono-O-acetylation appears to promote the crystallization of (II), inferred from the difficulty in crystallizing methyl β-d-mannopyranosyl-(1→3)-β-d-mannopyranoside despite repeated attempts. The conformational properties of the O-acetyl side chain in (II) are similar to those observed in recent studies of peracetylated mannose-containing oligosaccharides, having a preferred geometry in which the C2—H2 bond eclipses the C O bond of the acetyl group. The C2—O2 bond in (II) elongates by ≈0.02 ? upon O-acetylation. The phi (φ) and psi () torsion angles that dictate the conformation of the internal O-glycosidic linkage in (II) are similar to those determined recently in aqueous solution by NMR spectroscopy for unacetylated (II) using the statistical program MA'AT, with a greater disparity found for (? = ≈16°) than for φ (? = ≈6°).

Synthesis and O-Glycosidic Linkage Conformational Analysis of 13C-Labeled Oligosaccharide Fragments of an Antifreeze Glycolipid

NMR studies of two 13C-labeled disaccharides and a tetrasaccharide were undertaken that comprise the backbone of a novel thermal hysteresis glycolipid containing a linear glycan sequence of alternating [βXylp-(1→4)-βManp-(1→4)]n dimers. Experimental trans-glycoside NMR J-couplings, parameterized equations obtained from density functional theory (DFT) calculations, and an in-house circular statistics package (MA'AT) were used to derive conformational models of linkage torsion angles φ and ψ in solution, which were compared to those obtained from molecular dynamics simulations. Modeling using different probability distribution functions showed that MA'AT models of φ in βMan(1→4)βXyl and βXyl(1→4)βMan linkages are very similar in the disaccharide building blocks, whereas MA'AT models of ψ differ. This pattern is conserved in the tetrasaccharide, showing that linkage context does not influence linkage geometry in this linear system. Good agreement was observed between the MA'AT and MD models of ψ with respect to mean values and circular standard deviations. Significant differences were observed for φ, indicating that revision of the force-field employed by GLYCAM is probably needed. Incorporation of the experimental models of φ and ψ into the backbone of an octasaccharide fragment leads to a helical amphipathic topography that may affect the thermal hysteresis properties of the glycolipid.

Binding of the Bacterial Adhesin FimH to Its Natural, Multivalent High-Mannose Type Glycan Targets

Multivalent carbohydrate-lectin interactions at host-pathogen interfaces play a crucial role in the establishment of infections. Although competitive antagonists that prevent pathogen adhesion are promising antimicrobial drugs, the molecular mechanisms underlying these complex adhesion processes are still poorly understood. Here, we characterize the interactions between the fimbrial adhesin FimH from uropathogenic Escherichia coli strains and its natural high-mannose type N-glycan binding epitopes on uroepithelial glycoproteins. Crystal structures and a detailed kinetic characterization of ligand-binding and dissociation revealed that the binding pocket of FimH evolved such that it recognizes the terminal α(1-2)-, α(1-3)-, and α(1-6)-linked mannosides of natural high-mannose type N-glycans with similar affinity. We demonstrate that the 2000-fold higher affinity of the domain-separated state of FimH compared to its domain-associated state is ligand-independent and consistent with a thermodynamic cycle in which ligand-binding shifts the association equilibrium between the FimH lectin and the FimH pilin domain. Moreover, we show that a single N-glycan can bind up to three molecules of FimH, albeit with negative cooperativity, so that a molar excess of accessible N-glycans over FimH on the cell surface favors monovalent FimH binding. Our data provide pivotal insights into the adhesion properties of uropathogenic Escherichia coli strains to their target receptors and a solid basis for the development of effective FimH antagonists.

Structure-Based Design of a Monosaccharide Ligand Targeting Galectin-8

Galectin-8 is a β-galactoside-recognising protein that has a role in the regulation of bone remodelling and is an emerging new target for tackling diseases with associated bone loss. We have designed and synthesised methyl 3-O-[1-carboxyethyl]-β-d-galacto

Practical preparation of mono- and di-O-isopropylidene derivatives of monosaccharides and methyl 4,6-O-benzylidene glycosides from free sugars in a deep eutectic solvent

Free sugars were rapidly converted into the corresponding di-O-isopropylidene derivatives and methyl O-benzylidene glycosides in excellent yields and purity in a deep eutectic solvent made from choline chloride and malonic acid (ChCl:MA). Reaction conditions were mild; work-up was easy, and further purification was not necessary. Given the inexpensive, nontoxic, and recyclable nature of ChCl:MA, this protocol is environmental friendly.

A green and convenient method for regioselective mono and multiple benzoylation of diols and polyols

An efficient method for regioselective benzoylation of diols and polyols was developed. The benzoylation is catalyzed by only 0.2 equiv of benzoate anion in acetonitrile with the addition of a stoichiometric amount of benzoic anhydride under very mild condition, leading to high yields. Compared with all other methods, this method shows particular advantage in regioselective multiple benzoylation of polyols, and in avoiding the use of any metal-based catalysts and any amine bases, which is more environment-friendly.