51433-21-7

Usage

Uses

Used in Chemical Research:
Methyl 2-O,3-O-dimethyl-α-D-glucopyranosiduronic acid methyl ester is used as a precursor for the synthesis of various carbohydrate derivatives, making it a valuable tool in chemical research.
Used in Pharmaceutical Research:
Methyl 2-O,3-O-dimethyl-α-D-glucopyranosiduronic acid methyl ester is used as an important intermediate in the production of glycosidic compounds, which can be used as building blocks for the synthesis of various natural products and pharmaceuticals.
Used in Carbohydrate Chemistry:
Methyl 2-O,3-O-dimethyl-α-D-glucopyranosiduronic acid methyl ester is used in the study of carbohydrate chemistry due to its unique structure and properties.
Used in Drug Development:
Methyl 2-O,3-O-dimethyl-α-D-glucopyranosiduronic acid methyl ester is used in drug development as a building block for the synthesis of various pharmaceuticals.

Upstream product

• 10227-29-9 methyl 2,3-di-O-methyl-α-D-glucopyranoside 
• 18486-51-6 1-O-methyl-α-D-glucopyranuronic acid methyl ester 
• 74-88-4 methyl iodide 
• 186581-53-3 diazomethane 
• 907574-05-4 1,2,3-tri-O-methyl-α-D-glucopyranuronic acid 
• 67-56-1 methanol 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 3162-96-7 methyl 4,6-O-benzylidene-α-D-glucopyranoside 
• 3013-58-9 methyl 4,6-O-benzylidene-2,3-di-O-methyl-α,D-glucopyranoside 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 3013-58-9 methyl 4,6-O-benzylidene-2,3-di-O-methyl-α-D-glucopyranoside 

Downstream Products

• 63167-89-5 O¹,O²,O³-trimethyl-O⁴-(4-nitro-benzoyl)-α-D-glucopyranuronic acid methyl ester 

Relevant academic research and scientific papers

Differential reactivity of α- and β-anomers of glycosyl acceptors in glycosylations. A remote consequence of the endo-anomeric effect?

(equation presented) When phenyl tri-O-benzyl-1-thio-β-D-galactopyranosiduronic acid esters were coupled with a 1/1 mixture of a and β 2,3 di-O-protected D-galactopyranosiduronic acid esters, the β-anomer proved to be more reactive. Data from theoretical

From d-glucuronic acid to l-iduronic acid derivatives via a radical tandem decarboxylation-cyclization

A synthesis to l-iduronic derivatives, major components of heparin derived pentasaccharides was accomplished by formal inversion of configuration at C-5 of a d-glucuronic acid derivative through radical formation at C-5 using Barton decarboxylation followed by intramolecular radical addition on an acetylenic tether at O-4 giving exclusively a bicyclic sugar of l-ido configuration. Oxidation and ring opening of this bicyclic sugar led to a l-iduronate. This method opens the way to short syntheses of pentasaccharidic moiety of Idraparinux and congeners.

Process of preparation of L-iduronic acid comprising a decarboxylation/intramolecular cyclisation tandem reaction

The present invention relates to a process of preparation of L-iduronic acid and derivatives comprising a decarboxylation/intramolecular cyclisation tandem reaction. The present invention also relates to the intermediates of the process, as well as their use as intermediates in the preparation of Idraparinux.

PROCESS OF PREPARATION OF L-IDURONIC ACID AND DERIVATIVES COMPRISING A DECARBOXYLATION/INTRAMOLECULAR CYCLISATION TANDEM REACTION

The present invention relates to a process of preparation of L-iduronic acid and derivatives comprising a decarboxylation/intramolecular cyclisation tandem reaction. The present invention also relates to the intermediates of the process, as well as their use as intermediates in the preparation of Idraparinux.

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).

Regioselective methylation of methyl glycopyranosides with diazomethane in the presence of transition-metal chlorides and of boric acid

Partial methylation of the methyl pyranosides of a number of pentoses, hexoses, 6-deoxyhexoses, methyl uronates and their methyl ethers with diazomethane in the presence of transition-metal chlorides and boric acid was studied. It was found for methyl glycosides of pentoses and 6-deoxyhexoses that tin(II), antimony(III), and titanium(IV) chlorides as well as boric acid promoted substitution mainly of OH-3, but with cerium(III) and zinc(II) salts mainly substitution of OH-2 was observed. Methylation of methyl β-l-rhamnopyranoside demonstrated higher reactivity of OH-2 in all cases. The methylation of methyl glycosides of hexoses in the presence of tin(II), antimony(III) and cerium(III) chlorides gave mainly 3-methyl ethers. The 3-methyl ethers, which are not involved in further complexation, accumulated up to 50-80% of the reaction mixture (95-100% of monomethyl ether fraction). Convenient preparative syntheses of methyl ethers for a number of sugars are suggested. Copyright (C) 1999 Elsevier Science Ltd.

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.