17042-40-9

Usage

Uses

Used in Organic Chemistry Research:
4-Methoxyphenyl 2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranoside is used as a starting material for the synthesis of complex organic compounds. Its unique structure allows for the creation of a variety of molecules with potential applications in different fields.
Used in Biochemistry Research:
In biochemistry, 4-Methoxyphenyl 2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranoside is employed as an intermediate in the synthesis of biologically active molecules. Its acetylation pattern provides a means to control the reactivity of the molecule, which is crucial for the development of new biochemical agents.
Used in Pharmaceutical Industry:
4-Methoxyphenyl 2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranoside is used as a building block for the development of pharmaceutical compounds. Its ability to be modified and incorporated into larger molecules makes it a valuable tool in drug discovery and design.
Used in Chemical Modification:
4-METHOXYPHENYL 2,3,4,6-TETRA-O-ACETYL-ALPHA-D-MANNOPYRANOSIDE is used as a chemical modifier to alter the properties of other molecules. The presence of the acetyl groups on the mannopyranoside allows for selective chemical reactions, which can be harnessed to modify the reactivity and selectivity of other compounds in a controlled manner.
Used in Synthesis of Natural Products:
4-Methoxyphenyl 2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranoside is utilized in the synthesis of natural products, where its structural features can be employed to mimic or create complex natural molecules for various applications, including therapeutics and agrochemicals.
Each of these applications underscores the versatility and importance of 4-Methoxyphenyl 2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranoside in the realm of chemical and biochemical research and development.

InChI:InChI=1/C21H26O11/c1-11(22)27-10-17-18(28-12(2)23)19(29-13(3)24)20(30-14(4)25)21(32-17)31-16-8-6-15(26-5)7-9-16/h6-9,17-21H,10H2,1-5H3/t17-,18-,19+,20+,21+/m1/s1

Upstream product

• 6689-38-9 (4-methoxyphenoxy)trimethylsilane 
• 89825-07-0 1-O-trimethylsilyl-2,3,4,6-tetra-O-acetyl-D-glucoside 
• 150-76-5 4-methoxy-phenol 
• 439-03-2 2,3,4,6-tetra-O-acetyl-1-fluoro-α-D-glucopyranose 
• 604-69-3 β-D-glucose pentaacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 78942-85-5 2,3,4,6-tetra-O-acetyl-1-O-trifluoroacetyl-β-D-glucopyranose 
• 83-87-4 D-glucose pentaacetate 
• 74808-10-9 2,3,4,6-tetra-O-acetyl-d-glucopyranosyl trichloroacetimidate 
• 942428-83-3 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 4163-60-4 β-D-galactose peracetate 
• 25878-60-8 D-galactose pentaacetate 
• 74808-10-9 2,3,4,6-tetra-O-acetyl-D-galactopyranosyl trichloroacetimidate 

Downstream Products

• 4356-78-9 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl chloride 
• 38184-10-0 phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 62774-37-2 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-glucopyranoside 
• 67525-68-2 4'-Methoxyphenyl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 1200-06-2 4-methoxyphenyl acetate 
• 1075709-09-9 1-O-p-methoxyphenyl 6-O-tert-butyldiphenylsilyl-β-D-glucopyranose 
• 1004771-43-0 4-methoxyphenyl 2,3,4-tri-O-acetyl-β-D-glucopyranoside 
• 3150-20-7 4-methoxyphenyl β-D-galactopyranoside 
• 13992-16-0 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-galactopyranoside 
• 13992-16-0 1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 144985-19-3 p-methoxyphenyl 3-O-allyl-β-D-galactopyranoside 
• 105260-62-6 p-methoxyphenyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside 
• 1593082-63-3 4-methoxyphenyl 3-O-acetyl-6-azido-2,4-diacetamido-2,4,6-trideoxy-β-D-mannopyranoside 

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.

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.

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

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 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.

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.

Tea leaf perfumery precursor glucoside and synthesizing method thereof

The invention relates to a tea leaf perfumery precursor glucoside and a synthesizing method thereof. The synthesizing method comprises the following steps of synthesizing ten glucosides including aromatic alcohol ( alkanol )-beta -D-glucosides and aromatic alcohol (alkanol )-beta -D-primrose indicans. The synthesizing method disclosed by the invention is a glucoside synthesizing method which is good in selectivity, high in production rate and low in cost.

Method for chemically synthesizing beta-arbutin

The invention provides a method for chemically synthesizing beta-arbutin. The synthesis method includes the following steps: using D-glucose and acetic anhydride as raw materials, and carrying out reaction under the catalysis of molecular iodine to obtain a penta-acetyl glucose anomer mixture; subjecting the mixture without isolation and 4-Methoxyphenol to reaction under the catalysis of boron trifluoride diethyl etherate to obtain 4-Methoxyphenyl-2,3,4,6-Tetra-O-acetyl-beta-D-glucopyanoside, dissolving the 4-Methoxyphenyl-2,3,4,6-Tetra-O-acetyl-beta-D-glucopyanoside in anhydrous methanol, andremoving the acetyl group on the sugar ring and the methoxy group on the benzene ring under the conditions of sodium methoxide and cuprous oxide, thereby obtaining beta-arbutin. The method has the advantages of convenient operation, less discharge of the three wastes (waste gas, waste water and industrial residue), high yield and low cost, and the method is suitable for industrial production.

4-Methyltetrahydropyran (4-MeTHP): Application as an Organic Reaction Solvent

4-Methyltetrahydropyran (4-MeTHP) is a hydrophobic cyclic ether with potential for industrial applications. We herein report, for the first time, a comprehensive study on the performance of 4-MeTHP as an organic reaction solvent. Its broad application to organic reactions includes radical, Grignard, Wittig, organometallic, halogen-metal exchange, reduction, oxidation, epoxidation, amidation, esterification, metathesis, and other miscellaneous organic reactions. This breadth suggests 4-MeTHP can serve as a substitute for conventional ethers and harmful halogenated solvents. However, 4-MeTHP was found incompatible with strong Lewis acids, and the C?O bond was readily cleaved by treatment with BBr3. Moreover, the radical-based degradation pathways of 4-MeTHP, THP and 2-MeTHF were elucidated on the basis of GC-MS analyses. The data reported herein is anticipated to be useful for a broad range of synthetic chemists, especially industrial process chemists, when selecting the reaction solvent with green chemistry perspectives.

Selective acetolysis of primary benzyl groups in carbohydrate derivatives under the mild reaction condition

Selective acetolysis of the primary benzyloxy groups in a wide variety of carbohydrate derivatives was achieved in excellent yield using acetic anhydride and perchloric acid supported over silica (HClO4–SiO2) as a solid acid catalyst