2-O-Methyl-D-glucopyranose

Base Information

• Chemical Name: 2-O-Methyl-D-glucopyranose
• CAS No.: 2140-41-2
• Molecular Formula: C7H14 O6
• Molecular Weight: 194.185
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID90552826
• Nikkaji Number: J835.845A
• Mol file: 2140-41-2.mol

Synonyms:2140-41-2;2-O-METHYL-D-GLUCOPYRANOSE;D-Glucopyranose,2-O-methyl-;(3R,4S,5S,6R)-6-(hydroxymethyl)-3-methoxyoxane-2,4,5-triol;8-methylglucose;SCHEMBL78631;D-Glucopyranose, 2-O-methyl-;DTXSID90552826;UMPNFVHHMOSNAC-WLDMJGECSA-N;(3R, 4S, 5S, 6R)-6-(hydroxymethyl)-3-methoxyoxane-2, 4, 5-triol;(3R,4S,5S,6R)-6-(Hydroxymethyl)-3-methoxytetrahydro-2H-pyran-2,4,5-triol

Chemical Property of 2-O-Methyl-D-glucopyranose

Chemical Property:

• PSA: 99.38000
• LogP: -2.56730
• XLogP3: -2.1
• 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% ^*data from raw suppliers

2-O-Methyl-D-glucose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1C(C(C(OC1O)CO)O)O
• Isomeric SMILES: CO[C@@H]1[C@H]([C@@H]([C@H](OC1O)CO)O)O

Technology Process of 2-O-Methyl-D-glucopyranose

There total 2 articles about 2-O-Methyl-D-glucopyranose 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:

4-nitrophenyl 2-O-methyl-β-D-glucopyranoside (107150-81-2) → 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + 2-O-methyl-D-glucopyranose (2140-41-2)

Guidance literature:

With borate buffer (20percent free base); In water; at 80 ℃; Rate constant; var. buffers;

Reference yield:

glucomannan isolated from spruce → 2,3,6-tri-O-methyl-D-mannose (16742-38-4) + 2-O-methyl-D-glucopyranose (2140-41-2) + 2,6-di-O-methyl-D-glucose (90364-51-5) + 6-O-methyl-D-mannopyranose (10287-49-7,14199-58-7,24436-14-4,31505-26-7,31505-27-8,31505-28-9,31505-29-0,87936-86-5,87936-87-6,27552-12-1) + 2,3-di-O-methylmannopyranose (16742-44-2)

Guidance literature:

glucomannan isolated from spruce; With lithium isopropenolate; methyl iodide; In water; at 20 ℃; Inert atmosphere;

With trifluoroacetic acid; at 120 ℃; for 2h;

DOI:10.1016/j.carres.2014.06.005

Reference yield:

2-O-methyl-D-glucopyranose (2140-41-2) → 3-O-benzyl-6-deoxy-2-O-methyl-D-galactose diethyldithioacetal (87256-58-4)

Guidance literature:

Multi-step reaction with 9 steps

1: HCl / Heating

2: toluene-p-sulfonic acid / acetonitrile

3: NaH / tetrahydrofuran

4: aq. acetic acid / Heating

5: pyridine

6: lithium aluminium hydride / tetrahydrofuran / Heating

7: PCC / CH₂Cl₂ / Heating

8: NaBH₄ / methanol

9: 1.) trifluoracetic acid 2.) HCl / 1.) water 2.) CH₂Cl₂, 0 deg C

With pyridine; hydrogenchloride; sodium tetrahydroborate; lithium aluminium tetrahydride; sodium hydride; toluene-4-sulfonic acid; acetic acid; pyridinium chlorochromate; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;

upstream raw materials:

4-nitrophenyl 2-O-methyl-β-D-glucopyranoside

Downstream raw materials:

2-O-methylglucitol

methyl 3-O-benzyl-6-deoxy-2-O-methyl-α-D-glucopyranoside

methyl 3-O-benzyl-2-O-methyl-α-D-glucopyranoside

3-O-benzyl-6-deoxy-2-O-methyl-D-galactose diethyldithioacetal

Refernces

• 1、 Camilleri, Patrick,Jones, Rosie F. D.,Kirby, Anthony J.,Stroemberg, Roger. "Nucleophilic Catalysis of Glycoside Hydrolysis. The Hydrolysis of 4-Nitrophenyl α- and β-D-glucopyranoside Tetraphosphates". . p. 2085 - 2090. Retrieved 2007/10/02.