Methyl D-glucopyranoside

Base Information

• Chemical Name: Methyl D-glucopyranoside
• CAS No.: 3149-68-6
• Deprecated CAS: 26264-15-3,7539-03-9,7539-03-9
• Molecular Formula: C₇H₁₄O₆
• Molecular Weight: 194.185
• European Community (EC) Number: 221-581-9,246-894-8
• UNII: 54L5T38NI8
• DSSTox Substance ID: DTXSID4027523
• Nikkaji Number: J250.439A
• Wikipedia: Methylglucoside
• Wikidata: Q6824001
• Metabolomics Workbench ID: 55653
• Mol file: 3149-68-6.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 D-glucopyranoside

Chemical Property:

• Vapor Pressure: 1.15E-07mmHg at 25°C
• 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
• 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:

99.9% ^*data from raw suppliers

MethylD-Glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1C(C(C(C(O1)CO)O)O)O
• Isomeric SMILES: COC1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
• Uses: Methyl D-Glucopyranoside was studied for its possibility to be used as drilling fluids due to it being more environmentally friendly.

Technology Process of Methyl D-glucopyranoside

There total 200 articles about Methyl 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: 99.0%

tert-Butyl-diphenyl-((2R,3R,4S,5R)-3,4,5-tris-benzyloxymethoxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-silane → methyl D-glucopyranoside (97-30-3,617-04-9,709-50-2,1824-94-8,2152-78-5,3396-99-4,6819-48-3,18469-06-2,20550-04-3,22277-65-2,29411-57-2,35437-40-2,35437-43-5,36191-11-4,36191-12-5,39598-79-3,39598-80-6,39598-89-5,51023-63-3,51223-62-2,51224-38-5,51224-39-6,51224-40-9,51224-41-0,51819-81-9,51819-82-0,51819-83-1,56688-81-4,62279-53-2,64281-79-4,64281-80-7,64912-19-2,66101-73-3,78184-90-4,84368-39-8,84368-40-1,84368-41-2,92142-37-5,93302-26-2,103421-28-9,115794-08-6,3149-68-6)

Guidance literature:

With methanol; bromine; for 0.333333h; Heating;

DOI:10.1055/s-2001-15136

Reference yield: 90.0%

methanol (67-56-1) + D-glucose ethylene dithioacetal (3650-65-5) → methyl D-glucopyranoside (97-30-3,617-04-9,709-50-2,1824-94-8,2152-78-5,3396-99-4,6819-48-3,18469-06-2,20550-04-3,22277-65-2,29411-57-2,35437-40-2,35437-43-5,36191-11-4,36191-12-5,39598-79-3,39598-80-6,39598-89-5,51023-63-3,51223-62-2,51224-38-5,51224-39-6,51224-40-9,51224-41-0,51819-81-9,51819-82-0,51819-83-1,56688-81-4,62279-53-2,64281-79-4,64281-80-7,64912-19-2,66101-73-3,78184-90-4,84368-39-8,84368-40-1,84368-41-2,92142-37-5,93302-26-2,103421-28-9,115794-08-6,3149-68-6)

Guidance literature:

With iodine; for 18h; Heating;

DOI:10.1016/S0040-4039(00)83890-3

Reference yield:

azukisaponin I (82793-02-0) → methyl glucopyranosiduronic acid (4356-84-7,5155-45-3,5155-53-3,5241-02-1,5391-16-2,18486-39-0,46325-26-2,46325-27-3,73410-95-4,99094-38-9,134355-30-9,135414-77-6) + methyl D-glucopyranoside (97-30-3,617-04-9,709-50-2,1824-94-8,2152-78-5,3396-99-4,6819-48-3,18469-06-2,20550-04-3,22277-65-2,29411-57-2,35437-40-2,35437-43-5,36191-11-4,36191-12-5,39598-79-3,39598-80-6,39598-89-5,51023-63-3,51223-62-2,51224-38-5,51224-39-6,51224-40-9,51224-41-0,51819-81-9,51819-82-0,51819-83-1,56688-81-4,62279-53-2,64281-79-4,64281-80-7,64912-19-2,66101-73-3,78184-90-4,84368-39-8,84368-40-1,84368-41-2,92142-37-5,93302-26-2,103421-28-9,115794-08-6,3149-68-6) + sophoradiol (6822-47-5)

Guidance literature:

With hydrogenchloride; methanol; silver carbonate; for 2h; Heating;

DOI:10.1248/cpb.31.674

upstream raw materials:

methyl beta-D-galactopyranoside

Methyl mannoside

methyl beta-D-glucopyranoside

1-(trimethylsilyl)-1H-pyrrole

Downstream raw materials:

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

methyl 2,3,4,6-tetra-O-benzoyl-α-D-glycopyranoside

2,3,4-tri-O-benzoyl-5,6-dideoxy-L-arabino-hex-5-enose

C₂₇H₂₅NO₇

Refernces

• 1、 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.
• 2、 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.