35510-38-4

Basic information

• Product Name: 2,3,4,6-tetra-O-methyl-D-glucono-1,5-lactone
• Synonyms: 2,3,4,6-tetra-O-methyl-D-glucono-1,5-lactone
• CAS NO: 35510-38-4
• Molecular Weight: 234.249
• Mol File: 35510-38-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2,3,4,6-tetra-O-methyl-D-glucono-1,5-lactone(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-tetra-O-methyl-D-glucono-1,5-lactone(35510-38-4)
• EPA Substance Registry System: 2,3,4,6-tetra-O-methyl-D-glucono-1,5-lactone(35510-38-4)

Safety Data

• Hazardous Substances Data: 35510-38-4(Hazardous Substances Data)

Upstream product

• 908576-09-0 3.4.6-trimethyl-l-mannonic acid δ lactone 
• 74-88-4 methyl iodide 
• 103260-49-7 3.4.6-trimethyl-l-gluconic acid δ lactone 
• 3615-47-2 2,3,4,6-tetra-O-methyl-D-glucose 

Downstream Products

• 51224-21-6 2,3,4,6-tetra-O-methyl-D-mannono-1,5-lactone 
• 286860-94-4 1,2-[2',6'-di-O-benzyl-3-O-(3'',4'',5'',7''-tetra-O-methyl-1''-deoxy-1''-ethylsulfonato-α-D-gluco-hept-2''-ulopyranosyl)-β-D-galactopyranosyloxy]-(2,3,4-tri-O-benzyl-α-L-fucopyranosyloxy)ethane 
• 1198-69-2 D-glucono-1,4-lactone 

Relevant articles and documents

OXIDATION OF 2,3,4,6-TETRA-O-METHYL-D-GLUCOSE WITH ALKALINE HYDROGEN PEROXIDE

Treatment of 2,3,4,6-tetra-O-methyl-D-glucose with 10 molar equivalents of 30percent aqueous hydrogen peroxide and 2 molar equivalents of potassium hydroxide afforded, after chromatographic separation, 2,3,4,6-tetra-O-methyl-D-gluconolactone, 1-O-formyl-2,3,5-tri-O-methyl-D-arabinose methyl hemiacetal (7), 2,3,5-tri-O-methyl-D-arabinonolactone, methyl 2,3,5-tri-O-methyl-D-arabinoside, O-(2,4-di-O-methyl-D-erythrose)-(1'3)-2,4-di-O-methyl-D-erythronic acid, and O-(2,4-di-O-methyl-D-erythrose)-(1'2)-3-O-methyl-D-glyceraldehyde.The proportions of the products depended on the reaction conditions, especially the time, temperature, and the presence or absence of magnesium hydroxide.Formation of the products is explained by a series of reactions beginning with the addition of hydrogen peroxide to the carbonyl form of the methylated sugar.The adduct, with the help of superoxide radical and a molecule of hydrogen peroxide, breaks up in two ways, giving 2,3,4,6-tetra-O-methyl-D-gluconic acid and 7.The formic ester, on hydrolysis, gives 2,3,5-tri-O-methyl-D-arabinose, which undergoes a similar series of reactions, affording 2,3,5-tri-O-methyl-D-arabinonic acid, and presumably, 1-O-formyl-2,4-di-O-methyl-D-erythrose methyl hemiacetal.Apparently, the latter compound, on hydrolysis, forms a dimer, which, with alkaline hydrogen peroxide, undergoes a similar series of reactions, ultimately affording O-(2,4-di-O-methyl-D-erythrose)-(13)-2,4-di-O-methyl-D-erythronic acid and O-(2,4-di-O-methyl-D-erythrose)-(12)-3-O-methyl-D-glyceraldehyde.With a larger amount of alkali, under more-severe conditions, oxidation of 2,3,4,6-tetra-O-methyl-D-glucose proceeds further, with production of up to 3 moles of formic acid per mole of methylated sugar.