Methyl alpha-D-glucopyranoside

Base Information

• Chemical Name: Methyl alpha-D-glucopyranoside
• CAS No.: 97-30-3
• Deprecated CAS: 1321-19-3,15941-70-5,25281-47-4,25360-06-9,6817-79-4,1195722-83-8,15941-70-5,25281-47-4,25360-06-9,6817-79-4
• Molecular Formula: C7H14O6
• Molecular Weight: 194.185
• Hs Code.: 29321900
• European Community (EC) Number: 202-571-3
• UNII: QCF122NF3R
• DSSTox Substance ID: DTXSID7026605
• Nikkaji Number: J4.730I
• Wikidata: Q27074402
• Metabolomics Workbench ID: 52747
• ChEMBL ID: CHEMBL131853
• Mol file: 97-30-3.mol

Synonyms:1-O-methylglucose;alpha-methyl-D-glucopyranoside;alpha-methyl-D-glucoside;alpha-methylglucose;alpha-methylglucoside;alphaMG;beta-methyl-D-glucoside;beta-methylglucoside;D-glucoside, methyl;methyl alpha-D-glucopyranoside;methyl alpha-D-glucoside;methyl beta-D-glucopyranoside;methyl D-glucopyranoside;methyl D-glucoside;methyl glucose;methyl-alpha-D-glucoside;methyl-alpha-glucopyranoside;methyl-D-glucoside;methylglucoside;methylglucoside, (alpha-D)-isomer;methylglucoside, (beta-D)-isomer;methylglucoside, 13C-labeled;methylglucoside, 13C-labeled, (beta-D)-isomer;methylglucoside, 2H-labeled, (beta-D)-isomer;methylglucoside, 5-(17)O-labeled;methylglucoside, 6-(13)C-labeled;methylglucoside, 6-(17)O-labeled, (alpha-L)-isomer

Chemical Property of Methyl alpha-D-glucopyranoside

Chemical Property:

• Appearance/Colour: White Powder
• Vapor Pressure: 1.15E-07mmHg at 25°C
• Melting Point: 169-171 °C(lit.)
• Refractive Index: 157.5 ° (C=10, H2O)
• Boiling Point: 389.1 °C at 760 mmHg
• PKA: pKa (25°): 13.71
• Flash Point: 189.1 °C
• PSA: 99.38000
• Density: 1.47 g/cm³
• LogP: -2.56730
• Storage Temp.: Store at RT.
• Sensitive.: Hygroscopic
• Solubility.: Methanol (Slightly), Water (Slightly)
• Water Solubility.: 108 g/100 mL (20 ºC)
• 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-Glucopyranoside ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Other Organic Compounds
• 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
• Uses: manufacture of reconstituted and upgraded drying oils; tall oil esters and varnishes; fatty acid esters; plasticizers; nonionic surface active agents; fast and hard drying alkyd resins, and so-called plasticizing alkyds. In making glucoside hydroxypropyl ethers for polyurethan foam production. Methyl alpha-D-glucopyranoside is a biochemical used to vary echo decay times in a study that assessed the effects of cryoprotection on the structure and activity of p21ras. It is also used in a study to investigate saccharide-mediated protection of chaotropic-induced deactivation of concanavalin A.

Technology Process of Methyl alpha-D-glucopyranoside

There total 381 articles about Methyl alpha-D-glucopyranoside 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: 72.0%

cellulose (9004-34-6) → D-Fructose (57-48-7,18875-34-8) + D-glucose (50-99-7) + levulinic acid methyl ester (624-45-3) + methyl-alpha-D-glucopyranoside (97-30-3)

Guidance literature:

With aluminium acetylacetonate; toluene-4-sulfonic acid; In methanol; at 180 ℃; for 5h; under 3750.38 Torr; Reagent/catalyst; Temperature; Autoclave; Inert atmosphere;

DOI:10.1039/c6ra15638j

Reference yield: 62.0%

D-glucose (50-99-7) → D-Fructose (57-48-7,18875-34-8) + levulinic acid methyl ester (624-45-3) + methyl-alpha-D-glucopyranoside (97-30-3)

Guidance literature:

With aluminium acetylacetonate; toluene-4-sulfonic acid; In methanol; at 180 ℃; for 5h; under 3750.38 Torr; Reagent/catalyst; Autoclave; Inert atmosphere;

DOI:10.1039/c6ra15638j

Reference yield: 61.0%

methyl 2,3-di-O-methyl-α-D-glucopyranoside (10227-29-9,14048-30-7,22323-70-2,22323-71-3,23397-51-5,27299-05-4,31085-63-9,66808-29-5,66808-32-0,74560-65-9,91176-73-7,94992-18-4,110416-07-4) → D-sorbitol (50-70-4) + methyl-alpha-D-glucopyranoside (97-30-3)

Guidance literature:

With lithium; In ethylenediamine; for 0.5h; Product distribution;

DOI:10.1016/0008-6215(87)80028-9

upstream raw materials:

methanol

D-glucose

D-Glucose-dibenzyldithioacetal

diazomethane

Downstream raw materials:

1-O-methyl-α-D-glucopyranuronic acid methyl ester

Methyl-<4,6-dichlor-bis-O-(toluol-4-sulfonyl)-4,6-didesoxy-α-D-galactopyranosid>

methyl-[4-chloro-tris-O-(toluene-4-sulfonyl)-4-deoxy-α-D-galactopyranoside]

methyl-[tetrakis-O-(toluene-4-sulfonyl)-α-D-glucopyranoside]

Refernces

• 1、 Wang, Shao-Min,Zhu, Wei-Guo,Kang, Jian-Xun,Liu, Hong-Min,Chen, Jun-Miao,Li, Cui-Ping,Zhang, Kai. "ESIMS and NMR studies on the selective deprotection of acetylated glucosides by dibutyltin oxide". . p. 203 - 209. Retrieved 2011.
• 2、 Axelsson, Anton,Ta, Linda,Sundén, Henrik. "Direct Highly Regioselective Functionalization of Carbohydrates: A Three-Component Reaction Combining the Dissolving and Catalytic Efficiency of Ionic Liquids". . p. 3339 - 3343. Retrieved 2016.
• 3、 Kaulpiboon, Jarunee,Rudeekulthamrong, Prakarn. "Biosynthesis of methyl glucoside and its antibacterial activity against Staphylococcus aureus and Escherichia coli". . . Retrieved 2019.
• 4、 Rodebaugh, Robert,Debenham, John S.,Fraser-Reid, Bert. "Debenzylation of complex oligosaccharides using ferric chloride". . p. 5477 - 5478. Retrieved 1996.
• 5、 Wolfrom,Waisbrot. "". . p. 1408. Retrieved 1939.
• 6、 Rasool, Javeed Ur,Kumar, Atul,Ali, Asif,Ahmed, Qazi Naveed. "Triethylamine-methanol mediated selective removal of oxophenylacetyl ester in saccharides". . p. 338 - 347. Retrieved 2021/01/29.
• 7、 Chen, Kuanwei,Xie, Tao,Shen, Yanfang,He, Haibing,Zhao, Xiaoli,Gao, Shuanhu. "Calixanthomycin A: Asymmetric Total Synthesis and Structural Determination". supporting information. p. 1769 - 1774. Retrieved 2021/03/08.