Methyl alpha-D-mannopyranoside

Base Information

• Chemical Name: Methyl alpha-D-mannopyranoside
• CAS No.: 617-04-9
• Deprecated CAS: 25281-48-5,27939-30-6,882174-80-3
• Molecular Formula: C7H14O6
• Molecular Weight: 194.185
• Hs Code.: 29400090
• European Community (EC) Number: 210-502-3
• DSSTox Substance ID: DTXSID10897266
• Nikkaji Number: J95.586H
• Wikidata: Q27093072
• Metabolomics Workbench ID: 52350
• ChEMBL ID: CHEMBL195368
• Mol file: 617-04-9.mol

Synonyms:alpha-methyl-D-mannose;alpha-methylmannose;alpha-methylmannoside;beta-methylmannoside;methyl alpha-D-mannopyranoside;methyl beta-D-mannopyranoside;methyl D-mannopyranoside;methyl mannoside;methyl mannoside, (alpha-D)-isomer;methyl-alpha-D-mannoside;methylmannose;methylmannoside;methylmannoside, alpha-D-isomer

Chemical Property of Methyl alpha-D-mannopyranoside

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 193-196 °C
• Refractive Index: 79.5 ° (C=4, H2O)
• Boiling Point: 389.1 °C at 760 mmHg
• PKA: 12.92±0.70(Predicted)
• Flash Point: 189.1 °C
• PSA: 99.38000
• Density: 1.47 g/cm³
• LogP: -2.56730
• Storage Temp.: Refrigerator
• Solubility.: H2O: 0.1 g/mL, clear
• Water Solubility.: It is easily soluble in methanol, water. Insoluble in ether.
• XLogP3: -2.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 194.07903816
• Heavy Atom Count: 13
• Complexity: 163

Purity/Quality:

98% ^*data from raw suppliers

Methyl a-D-Mannopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,F
• Hazard Codes: Xi,F
• Statements: 10
• Safety Statements: 22-24/25-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Monosaccharides and Derivatives
• Canonical SMILES: COC1C(C(C(C(O1)CO)O)O)O
• Isomeric SMILES: CO[C@@H]1[C@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
• General Description: Methyl α-D-mannopyranoside is a monosaccharide derivative that serves as a versatile starting material for the synthesis of σ-receptor ligands with potential therapeutic applications, including antipsychotic, antidepressant, anticocaine, and antitumor effects. Key structural modifications, such as the introduction of a dichlorophenylacetamide group at position 7 and equatorial amino substituents at position 3, were found to enhance σ1-receptor affinity and selectivity. The most promising compound derived from this scaffold exhibited high σ1-receptor binding (Ki = 21 nM), highlighting its potential as a lead structure for drug development.

Technology Process of Methyl alpha-D-mannopyranoside

There total 262 articles about Methyl alpha-D-mannopyranoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

methanol (67-56-1) + D-Mannose (530-26-7) → (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol (617-04-9)

Guidance literature:

With acetyl chloride; for 0.583333h; Heating; microwave irradiation;

DOI:10.1081/SCC-100104035

Reference yield: 97.0%

methanol (67-56-1) + D-Mannose (3458-28-4) → (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol (617-04-9)

Guidance literature:

With acetyl chloride; for 6h; Inert atmosphere; Reflux;

Reference yield: 95.0%

(2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran (3879-79-6,17791-37-6,19488-61-0,53008-63-2,69237-94-1,69237-95-2,71526-33-5,83462-67-3,84799-77-9,103421-29-0,103421-30-3,139241-42-2,61330-62-9) → (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol (617-04-9)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; ethyl acetate; at 80 ℃; under 30003 Torr; Continuous flow hydrogenotion reactor;

DOI:10.1016/j.tetlet.2010.12.109

upstream raw materials:

D-Mannose

Perbenzoic acid

ethyl acetate

D-glucal

Downstream raw materials:

(2S,3S,4S,5R,6R)-2-methoxy-6-((trityloxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

methyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside

methyl 2,3,4-tri-O-benzoyl-6-O-trityl-α-D-mannopyranoside

methyl 6-O-trityl-α-D-mannopyranoside

Refernces

Synthesis of novel σ-receptor ligands from methyl α-d-mannopyranoside

10.1016/j.carres.2006.06.016

The study focuses on the synthesis of novel σ-receptor ligands using methyl α-D-mannopyranoside as the starting material. This is the first time a monosaccharide has been utilized for the creation of such ligands, which have potential applications as antipsychotics, antidepressants, anticocaine agents, and antitumor agents. The researchers employed various chemicals in the synthesis process, including nitrile 7, which was transformed into hept-3-ulopyranoside dimethyl ketals 14 and 15 through two different synthetic routes. Amino substituents were introduced into position 3 after selective hydrolysis of the ketone dimethyl acetal. The study identified that a dichlorophenylacetamide moiety in position 7 and equatorially arranged amino substituents in position 3 were crucial for high σ1-receptor affinity and selectivity. The synthesized compounds were then tested for their affinity and selectivity towards σ1 and σ2 receptors, as well as their interaction with other receptor systems such as the phencyclidine binding site of the NMDA receptor, δ-opioid, and μ-opioid receptors. The most active compound in the series, an anomeric mixture of dimethylamines 26a/b, showed the highest σ1-receptor affinity with a Ki value of 21 nM. The study demonstrated the potential of using monosaccharides as building blocks for the development of new drugs with high σ1-receptor affinity and selectivity.

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