18486-51-6

Upstream product

• 186581-53-3 diazomethane 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 67-56-1 methanol 
• 17681-01-5 methyl β-D-glucofuranosidurono-6,3-lactone 
• 96553-02-5 methyl (28-Hydroxy-23,28-dioxoolean-12-en-3β-yl β-D-Glucopyranoside)uronate 
• 6556-12-3 D-glucuronic acid 
• 27531-18-6 O¹-methyl-α-D-glucopyranuronic acid amide 
• 5155-45-3 methyl α-D-glucopyranosiduronic acid 
• 77-76-9 2,2-dimethoxy-propane 
• 7647-01-0 hydrogenchloride 
• 74-88-4 methyl iodide 
• 643-33-4 D-galacturonic acid 
• 25577-38-2 methyl α-D-glucopyranosiduronate sodium salt 

Downstream Products

• 31506-19-1 methyl (methyl 3-O-methyl-α-D-glucopyranosid)uronate 
• 51433-24-0 (2S,3S,4S,5R,6S)-4-Hydroxy-3,5,6-trimethoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 31506-18-0 Methyl uronate 
• 52729-97-2 1,2,3,4-tetra-O-methyl-α-D-glucopyranuronic acid methyl ester 
• 51433-21-7 1,2,3-tri-O-methyl-α-D-glucopyranuronic acid methyl ester 
• 31506-20-4 (2S,3S,4S,5R,6S)-3,4-Dihydroxy-5,6-dimethoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 51433-28-4 (2S,3S,4R,5R,6S)-5-Hydroxy-3,4,6-trimethoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

3'-KETOGLYCOSIDE COMPOUND FOR THE SLOW RELEASE OF A VOLATILE ALCOHOL

The present invention relates to a 3'-ketoglycoside compound defined by formula (I) and its use for controlled release of alcohols, in particular alcohols showing an insect repellent effect. It relates also to a process for preparing the 3'-ketoglycoside compound of formula (I). It further relates to a composition comprising a 3'- ketoglycoside compound of formula (I). It relates also to the use of a 3'-ketoglycoside compound of formula (I) for the controlled release of alcohols. It related also to a method of use of such composition.

Electroorganic synthesis in oil-in-water (O/W) nanoemulsion: TEMPO-mediated electrooxidation of amphiphilic alcohols in water

Oil-in-water nanoemulsion which consisted of TEMPO, amphiphilic alcohols, and water offered unique reaction environments for electrooxidation of the alcohols to give the corresponding carboxylic acids in good to excellent yields.

Synthesis pathway to carbohydrate-derived salicylidene hydrazides as ligands for oxovanadium complexes

Salicylidene hydrazides represent important ligands forming oxovanadium complexes. Carbohydrate-derived chiral salicylidene hydrazides as ligands for metal ion complexation were synthesized for the first time. The pathway of the mild and selective synthesis starts from commercial saccharides like methyl-α-d-glucopyranoside and methyl-α-d-mannopyranoside. All synthesized carbohydrate-derived salicylidene hydrazides are able to form oxovanadium complexes. The mononuclear structure proposed for the complex of 1,2,3,4-tetra-O-methyl-α-d-glucopyranuronic acid salicylidene hydrazide is consistent with the analytical data (NMR, IR and MS).

Electroorganic synthesis 66: Selective anodic oxidation of carbohydrates mediated by TEMPO

The carbohydrates 4-15 are anodically oxidized with 2,2,6,6- tetramethylpiperidin-1-oxyl (TEMPO) as mediator. Selective and complete reaction at the primary hydroxyl groups affords the corresponding carboxylic acids 16-32 in moderate to excellent yield. Methyl α-D-glucopyranoside is converted in 98% yield to the uronic acid 16. Cyclic voltammetry shows that the oxydation is base-catalyzed and the oxidation of the hydroxy group with TEMPO+ (2) is rate determining.

Study on the Mechanism of Diazomethane Degradation of the Sugar-Aglycone Linkage in Gypsogenin 3-O-Glycoside

The mechanism of the diazomethane degradation of the sugar-aglycone linkage of the gypsogenin 3-O-glycoside (1) was studied.Since there are three kinds of functional groups in 1 - the 4α-aldehyde group in the aglycone, the carboxy, and the 4'-hydroxy group in the glucuronic acid - which are presumed to contribute to the degradation reaction, the role of each functional group was examined using synthesized model compounds.As a result of the study, only the 4α-aldehyde group was shown to be essential.By taking the above evidence and the reaction of aldehyde with diazomethane into account, the degradation is thought to proceed through an epoxide intermediate as shown in Scheme 6.The reaction of gypsogenin with diazomethane was also examined.

SYNTHESIS OF METHYL ETHERS OF METHYL (METHYL α-D-GLUCOPYRANOSID) URONATE

Methyl (methyl α-D-glucopyranoisid)uronate (I) has been obtained by the catalytic oxidation of methyl α-D-glucopyranoside with oxygen in the presence of platinum on carbon with a yield of 31percent.The partial methylation of (I) followed by preparative liquid column chromatography on silica gel has provided a convenient method of obtaining all the methyl ethers of (I) in the individual state.

METHANOLYSIS STUDIES OF CARBOHYDRATES, USING H.P.L.C.

An h.p.l.c. system that separates carbohydrates as their methyl glycosides has been used to study the products obtained on treatment of various carbohydrates with methanolic hydrogen chloride.Results are presented for the monosaccharide composition of several polysaccharides, lactone and ester formation during the treatment of D-glucuronic acid, and relative rates of glycosidation vs. esterification during the treatment of D-galacturonic acid.