28541-75-5

Usage

Uses

Used in Pharmaceutical Industry:
4-Methoxyphenyl alpha-D-mannopyranoside is used as a bioactive compound for its antimicrobial, antiviral, and anticancer properties. It contributes to the development of new drugs and therapies that can target a wide range of diseases and conditions.
Used in Medical Research:
In the field of medical research, 4-Methoxyphenyl alpha-D-mannopyranoside is utilized as a subject of study to explore its potential applications in treating various diseases. Its unique chemical structure and bioactive properties make it a valuable candidate for further investigation and development.
Used in Drug Development:
4-Methoxyphenyl alpha-D-mannopyranoside is employed as a key component in the formulation of new drugs. Its ability to target specific biological processes and pathways makes it a promising candidate for the development of innovative therapeutic agents.
Used in Natural Product Extraction:
In the natural product extraction industry, 4-Methoxyphenyl alpha-D-mannopyranoside is used as a valuable component extracted from plants and algae. Its presence in these natural sources highlights its potential as a source of bioactive compounds for various applications.
Used in Cosmetics Industry:
4-Methoxyphenyl alpha-D-mannopyranoside is utilized in the cosmetics industry for its potential skin health benefits. Its antimicrobial and antiviral properties may contribute to the development of skincare products that promote a healthy and radiant complexion.
Used in Food Industry:
In the food industry, 4-Methoxyphenyl alpha-D-mannopyranoside may be used as a natural preservative due to its antimicrobial properties. Its ability to inhibit the growth of harmful microorganisms can help extend the shelf life of food products and maintain their quality.
Used in Agricultural Industry:
4-Methoxyphenyl alpha-D-mannopyranoside can be employed in the agricultural industry as a natural pesticide or fungicide. Its bioactive properties can help protect crops from diseases and pests, promoting healthier and more sustainable agricultural practices.

InChI:InChI=1/C13H18O7/c1-18-7-2-4-8(5-3-7)19-13-12(17)11(16)10(15)9(6-14)20-13/h2-5,9-17H,6H2,1H3/t9-,10-,11+,12+,13+/m1/s1

Upstream product

• 150-76-5 4-methoxy-phenol 
• 2106-10-7 1-deoxy-1-fluoro-α-D-glucose 
• 447-27-8 β-D-glucopyranosyl fluoride 
• 17042-40-9 4-methoxyphenyl 2,3,4,6-tetra-O-acetyl-1-α-D-mannopyranoside 
• 530-26-7 D-Mannose 
• 4163-60-4 β-D-galactose peracetate 
• 2872-65-3 4-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 
• 604-68-2 α-D-glucopyranose peracetylate 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 83-87-4 D-glucose pentaacetate 
• 2280-44-6 D-Glucose 
• 2872-65-3 p-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 4336-91-8 3-bromo-2-pyridyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 

Downstream Products

• 854735-96-9 4-methoxyphenyl 4,6-O-cyclohexylidene-β-D-glucopyranoside 
• 1075709-09-9 1-O-p-methoxyphenyl 6-O-tert-butyldiphenylsilyl-β-D-glucopyranose 
• 180274-49-1 p-Methoxyphenyl 4,6-O-isopropylidene-β-D-glucopyranoside 
• 1140306-38-2 p-methoxyphenyl 2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 138889-19-7 4-methoxyphenyl 6-O-(4,4'-dimethoxytrityl)-β-D-galactopyranoside 
• 144985-19-3 p-methoxyphenyl 3-O-allyl-β-D-galactopyranoside 
• 159922-67-5 4-methoxyphenyl 3,4-O-isopropylidene-β-D-galactopyranoside 
• 212127-28-1 p-methoxyphenyl 3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-β-D-galactopyranoside 
• 473553-47-8 p-methoxyphenyl 4,6-O-(2-naphthyl)methylene-β-D-galactopyranoside 
• 503303-06-8 p-methoxyphenyl 6-O-tert-butyldiphenylsilyl-β-D-galactopyranoside 
• 774591-92-3 4-methoxyphenyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 4132-28-9 (3R,4R,5R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-ol 

Relevant academic research and scientific papers

Chemical synthesis and pharmacological properties of heparin pentasaccharide analogues

The pentasaccharide fondaparinux is a synthetic anticoagulant based on heparin antithrombin-binding sequence. Fondaparinux improves safety and predictable pharmacodynamics compared with heparins; however, it requires a complicate synthesis process which contain more than 50 steps of synthesis. Herein, we designed and synthesized four fondaparinux analogues (compounds 1, 2, 3, 4) using a [2+3] convergent synthetic method, which greatly simplified the synthetic process, improved the product yield, and curtailed the expenditures. These synthesized compounds showed stronger anticoagulant activities by factor Xa inhibition (IC50 725–1126 nM vs. 1909 nM for fondaparinux) in the AT-dependent manner. After subcutaneous (s.c.) administration to rats, the compounds displayed long-lasting anti-factor Xa activities and inhibition of thrombin generation ex vivo. Compared with fondaparinux, these compounds were slowly eliminated after s.c. administration to rats, the half-lies (t1/2) were more than 2-fold of that of fondaparinux. These results suggested the pentasaccharide analogues may exhibit better pharmacokinetic and predictable pharmacodynamic characteristics.

Chemoenzymatic Synthesis of Sialosides Containing 7- N- or 7,9-Di- N-acetyl Sialic Acid as Stable O-Acetyl Analogues for Probing Sialic Acid-Binding Proteins

A novel chemoenzymatic synthon strategy has been developed to construct a comprehensive library of α2-3- and α2-6-linked sialosides containing 7-N- or 7,9-di-N-acetyl sialic acid, the stable analogue of naturally occurring 7-O-acetyl- or 7,9-di-O-acetyl-s

Synthesis and conformational analysis of vicinally branched trisaccharide β-d-Galf-(1 → 2)-[β-d-Galf-(1 → 3)-]-α-GalpfromCryptococcus neoformansgalactoxylomannan

The synthesis of a vicinally branched trisaccharide composed of twod-galactofuranoside residues attachedviaβ-(1 → 2)- and β-(1 → 3)-linkages to the α-d-galactopyranoside unit has been performed for the first time. The reported trisaccharide represents the galactoxylomannan moiety first described in 2017, which is the capsular polysaccharide of the opportunistic fungal pathogenCryptococcus neoformansresponsible for life-threatening infections in immunocompromised patients. The NMR-data reported here for the synthetic model trisaccharide are in good agreement with the previously assessed structure of galactoxylomannan and are useful for structural analysis of related polysaccharides. The target trisaccharide as well as the constituent disaccharides were analyzed by a combination of computational and NMR methods to demonstrate good convergence of the theoretical and experimental results. The results suggest that the furanoside ring conformation may strongly depend on the aglycon structure. The reported conformational tendencies are important for further analysis of carbohydrate-protein interaction, which is critical for the host response towardC. neoformansinfection.

Synthesis of nature product kinsenoside analogues with anti-inflammatory activity

Kinsenoside is the major bioactive component from herbal medicine with a broad range of pharmacological functions. Goodyeroside A, an epimer of kinsenoside, remains less explored. In this report we chemically synthesized kinsenoside, goodyeroside A and their analogues with glycan variation, chirality inversion at chiral center(s), and bioisosteric replacement of lactone with lactam. Among these compounds, goodyeroside A and its mannosyl counterpart demonstrated superior anti-inflammatory efficacy. Furthermore, goodyeroside A was found to suppresses inflammatory through inhibiting NF-κB signal pathway, effectively. Structure-activity relationship is also explored for further development of more promising kinsenoside analogues as drug candidates.

Serendipitous one-pot synthesis of chiral dienes from pyranosidic 2,4-bistriflates

Attempted nucleophilic displacements of L-rhamnosyl 2,4-bistriflates led to serendipitous formation of a chiral diene via competing cascade eliminations. The reaction also followed the same pathway with D-rhamnosyl and D-mannosyl 2,4-bistriflates substrat

Solvent-Free Glycosylation from per-O-Acylated Donors Catalyzed by Methanesulfonic Acid

The huge importance of carbohydrates and their derivatives in biomedical and industrial applications call for the development of streamlined and sustainable procedures for their synthetic elaboration. Here reported a novel glycosylation method based on direct activation of readily available per-O-acylated (acetylated or benzoylated) donors, promoted under air by methanesulfonic acid as a cheap and green catalyst in the absence of any solvent. Besides the beneficial avoidance of toxic and polluting organic solvents, these conditions were found critical for activating such poorly reactive donors with a very small catalyst loading (only 5 mol %), instead of stoichiometric Lewis acid promoters typically employed. Desired glycosides were quickly obtained, in most cases with high 1,2-trans stereoselectivity. Other main advantages over reported glycosylations with similar donors are the limited stoichiometric excess of the acceptor (or the donor), the easy applicability and low cost of the procedure and the wide target scope, also covering the synthesis of disaccharides and other non-trivial glycosides with applicable potential.

Studies towards the total synthesis of repeating unit of O-sulfated polysaccharide from marine bacterium Cobetia pacifica KMM 3878

Herein we report assembly of the appropriately protected trisaccharide repeating unit of Cobetia pacifica KMM 3878 O-sulfated polysaccharide. Our synthesis involves 3,4-O-pyruvilated galactose as the key building block which acts as a donor as well as acceptor in the construction of trisaccharide. We obtained the R isomer as a major stereoisomer in the pyruvilation reaction. The glycosylations proceeded with high stereo and regioselectivity.

Scope of the DMC mediated glycosylation of unprotected sugars with phenols in aqueous solution

Activation of reducing sugars in aqueous solution using 2-chloro-1,3-dimethylimidazolinium chloride (DMC) and triethylamine in the presence of para-nitrophenol allows direct stereoselective conversion to the corresponding 1,2-Trans para-nitrophenyl glycosides without the need for any protecting groups. The reaction is applicable to sulfated and phosphorylated sugars, but not to ketoses or uronic acids or their derivatives. When applied to other phenols the product yield was found to depend on the pKa of the added phenol, and the process was less widely applicable to 2-Acetamido sugars. For 2-Acetamido substrates an alternative procedure in which the glycosyl oxazoline was pre-formed, the reaction mixture freeze-dried, and the crude product then reacted with an added phenol in a polar aprotic solvent system with microwave irradiation proved to be a useful simplification.

Regio/Stereoselective Glycosylation of Diol and Polyol Acceptors in Efficient Synthesis of Neu5Ac-α-2,3-LacNPhth Trisaccharide

A concise approach to a Neu5Ac-α-2,3-LacNPhth trisaccharide derivative was developed. First, the regio/stereoselective glycosylation between glycoside donors and glucoNPhth diol acceptors was investigated. It was found that the regioselectivity depends not only on the steric hindrance of the C2-NPhth group and the C6-OH protecting group of the glucosamine acceptors, but also on the leaving group and protecting group of the glycoside donors. Under optimized conditions, LacNPhth derivatives were synthesized in up to 92 % yield through a regio/stereoselective glycosylation between peracetylated-α-galactopyranosyl trichloroacetimidate and p-methoxyphenyl 6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-β-d-glucopyranoside, avoiding the formation of glycosylated orthoesters and anomeric aglycon transfer. Then, the LacNPhth derivative was deacylated and then protected on the primary position by TBDPS to form a LacNPhth polyol acceptor. Finally, the Neu5Ac-α-2,3-LacNPhth derivative was synthesized in 48 % yield through the regio/stereoselective glycosylation between the LacNPhth polyol acceptor and a sialyl phosphite donor. Starting from d-glucosamine hydrochloride, the target Neu5Ac-α-2,3-LacNPhth derivative was synthesized in a total yield of 18.5 % over only 10 steps.

Synthesis method of core structure of O-mannan

The invention belongs to the field of synthesis of saccharide substances, and particularly relates to a synthesis method of the core structure of O-mannan. Conventional research indicates that alpha-DG O-mannan is relevant with a mechanism of diseases of