Methyl beta-D-glucopyranoside

Base Information

• Chemical Name: Methyl beta-D-glucopyranoside
• CAS No.: 709-50-2
• Deprecated CAS: 27939-29-3,30326-25-1,75398-85-5
• Molecular Formula: C7H14O6
• Molecular Weight: 194.185
• Hs Code.: 29389090
• European Community (EC) Number: 211-909-9
• DSSTox Substance ID: DTXSID20883559
• Nikkaji Number: J109.292H
• Wikidata: Q27092822
• Metabolomics Workbench ID: 52746
• ChEMBL ID: CHEMBL132186
• Mol file: 709-50-2.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 beta-D-glucopyranoside

Chemical Property:

• Appearance/Colour: White Cyrstalline Solid
• Melting Point: 107-111ºC
• Refractive Index: 1.548
• 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.: -20?C Freezer, Under Inert Atmosphere
• Solubility.: H2O: 0.1 g/mL, clear, colorless
• Water Solubility.: 367.4g/L(17 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 b-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:

• 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: Methyl β-D-Glucopyranoside (cas# 709-50-2) is a compound useful in organic synthesis.

Technology Process of Methyl beta-D-glucopyranoside

There total 330 articles about Methyl beta-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: 95.0%

methanol (67-56-1) + pyridin-2-yl 1-thio-β-D-glucopyranoside (2297-41-8) → 2-Sulfanylpyridine (2637-34-5,73018-10-7) + methyl beta-D-glucopyranoside (709-50-2)

Guidance literature:

With citrate-phosphate buffer; almond β-D-glucosidase; at 25 ℃; for 1h; pH=5.0;

Reference yield: 11.0%

methanol (67-56-1) + cellulose (9004-34-6) → levulinic acid methyl ester (624-45-3) + methyl beta-D-glucopyranoside (709-50-2) + methyl-alpha-D-glucopyranoside (97-30-3)

Guidance literature:

With H-meso-ZSM-5; at 189.84 ℃; for 18h; under 22502.3 Torr; Catalytic behavior; Autoclave;

DOI:10.1016/j.cattod.2016.01.055

Reference yield:

methanol (67-56-1) + cellulose (9004-34-6) → 5-(methoxymethyl)-2-furaldehyde (1917-64-2) + β-D-glucose (492-61-5) + levulinic acid methyl ester (624-45-3) + methyl beta-D-glucopyranoside (709-50-2)

Guidance literature:

With aluminum(III) sulfate; water; at 180 ℃; for 6h; Kinetics; Green chemistry;

DOI:10.1039/c7gc02883k

upstream raw materials:

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

methyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

diazomethane

β-anomer of trideca-O-methylpedunculagin

Downstream raw materials:

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

methyl 2,3,4-tri-O-acetyl-6-O-trityl-β-D-glucopyranoside

Methyl 6-O-triphenylmethyl-β-D-glucopyranoside

methyl-(tetrakis-O-phenylcarbamoyl-β-D-glucopyranoside)

Refernces

• 1、 Naganawa,Usui,Takita,et al.. "4 amino 4 deoxy α,α trehalose, a new metabolite of a streptomyces". . p. 145 - 146. Retrieved 1974.
• 2、 Nakano, Kimiko,Nishizawa, Koji,Murakami, Kotaro,Takaishi, Yoshihisa,Tomimatsu, Toshiaki. "STEROIDAL ALKALOID GLYCOSIDES FROM LILIUM CORDATUM". . p. 301 - 304. Retrieved 1987.
• 3、 Qian-Cutrone, Jingfang,Ueki,Huang, Stella,Mookhtiar, Kasim A.,Ezekiel, Regina,Kalinowski, Steven S.,Brown, Karen S.,Golik, Jerzy,Lowe, Susan,Pirnik, Dolores M.,Hugill, Robert,Veitch, Judy A.,Klohr, Steven E.,Whitney, Jeffrey L.,Manly, Susan P.. "Glucolipsin A and B, two new glucokinase activators produced by Streptomyces purpurogeniscleroticus and Nocardia vaccinii". . p. 245 - 255. Retrieved 1999.
• 4、 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.
• 5、 Bertella, Anis,Bitam, Fatma,Carbone, Marianna,Ciavatta, Maria Letizia,Gavagnin, Margherita,Smadi, Abla. "Chemical constituents of the aerial parts of Algerian Galium brunneum: Isolation of new hydroperoxy sterol glucosyl derivatives". . p. 39 - 45. Retrieved 2020/05/25.