D-Glucose, 4-O-methyl-

Base Information

• Chemical Name: D-Glucose, 4-O-methyl-
• CAS No.: 4132-38-1
• Molecular Formula: C7H14O6
• Molecular Weight: 194.185
• Hs Code.: 2912499000
• Mol file: 4132-38-1.mol

Synonyms:D-Glucose, 4-O-methyl-;4-O-Methyl-D-glucose

Chemical Property of D-Glucose, 4-O-methyl-

Chemical Property:

• PSA: 107.22000
• LogP: -2.72470

Purity/Quality:

95% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: **4-O-Methyl-D-glucose** is a methylated derivative of D-glucose where the hydroxyl group at the C-4 position is substituted with a methoxy group. In the context of the study, it served as a substrate for oxidation with 2-anthraquinonesulfonic acid, yielding products such as erythronic, arabinonic, ribonic, gluconic, and mannonic acids, as well as 2-C-carboxypentoses, indicating its reactivity under alkaline oxidative conditions. The presence of the 4-O-methyl group influences its degradation pathway compared to unsubstituted D-glucose, leading to distinct oxidation products.

Technology Process of D-Glucose, 4-O-methyl-

There total 13 articles about D-Glucose, 4-O-methyl- 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:

β-D-4-O-methylglucopyranoside (31505-22-3) → O4-methyl-D-glucose (4132-38-1)

Guidance literature:

With hydrogenchloride; at 100 ℃;

DOI:10.1016/S0008-6215(00)90462-2

Reference yield:

O4-methyl-β-D-1,6-anhydro-glucopyranose → O4-methyl-D-glucose (4132-38-1)

Guidance literature:

With sulfuric acid; at 100 ℃; for 4h;

Reference yield:

methyl 4-O-methyl-β-D-glucopyranoside (3056-43-7) → O4-methyl-D-glucose (4132-38-1)

Guidance literature:

With sulfuric acid;

DOI:10.1139/v54-004

upstream raw materials:

O³,O⁶-diacetyl-O⁴-methyl-O¹,O²-phenanthrene-9,10-diyl-ξ-D-glucopyranose

methyl 4-O-methyl-β-D-glucopyranoside

methyl 4-O-methyl-α-D-glucopyranoside

O⁴-methyl-D-glucuronic acid

Downstream raw materials:

O⁴-methyl-D-gluconic acid-5-lactone

benzyl-(O²,O³,O⁶-triacetyl-O⁴-methyl-β-D-glucopyranoside)

O⁴-methyl-D-arabino-[2]hexosulose-bis-phenylhydrazone

α-isosaccharinic acid

Refernces

2-C-CARBOXYALDOSES AND ALDONIC ACIDS FROM CELLOBIOSE, MALTOSE, AND 4-O-METHYL-D-GLUCOSE WITH 2-ANTHRAQUINONESULFONIC ACID

10.1016/S0008-6215(00)90462-2

The research details an investigation into the oxidation of cellobiose, maltose, and 4-O-methyl-D-glucose using 2-anthraquinonesulfonic acid (AMS) in sodium hydroxide. The purpose of the study was to gain insights into the reactions of aldoses, specifically aldos-2-uloses, by subjecting these 4-O-substituted aldoses to oxidation conditions similar to those used for D-glucose. The research concluded that the oxidation products included erythronic, arabinonic, ribonic, gluconic, and mannonic acids, as well as 2-C-carboxypentoses, which were identified as a new type of product in the reaction mixture. The study also found that the nonsubstituted products of the reducing D-glucose unit consisted of formic, glycolic, 2-deoxytetronic, and 3-deoxypentonic acids, along with 2-C-carboxy-3-deoxypentoses. The chemicals used in the process included 2-anthraquinonesulfonic acid as the oxidizing agent, sodium hydroxide to maintain the reaction conditions, and various sugars as substrates for the oxidation reactions.

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