18486-53-8Relevant academic research and scientific papers
Electroorganic synthesis 66: Selective anodic oxidation of carbohydrates mediated by TEMPO
Schnatbaum, Karsten,Sch?fer, Hans J.
, p. 864 - 872 (1999)
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.
Synthesis, characterization, and crystal structure of sodium (methyl α- D -mannopyranosid)uronate monohydrate
Xu, Peng,Dauter, Zbigniew,Kovac, Pavol
, p. 1073 - 1078 (2014)
TEMPO (2,2,6,6-tetramethylpiperidine-1-oxyl)-mediated oxidation of methyl α-d-mannopyranoside with sodium hypochlorite gave sodium (methyl α-d-mannopyranosid)uronate, which was obtained as a crystalline monohydrate in ~70% yield without chromatography. Its purity was proved by NMR spectroscopy, a newly developed HPLC method, combustion analysis, and X-ray crystallography. The crystal structure, solved from synchrotron diffraction data in space group P212121, revealed that the packing of the uronate molecules is connected by an extensive network of hydrogen bonds, and that the Na+ ion is coordinated by six oxygen ligands from one water and three surrounding sugar molecules. Georg Thieme Verlag Stuttgart New York.
Enantioselective de novo synthesis of 4-deoxy-d-hexopyranoses via hetero-Diels-Alder cycloadditions: Total synthesis of ezoaminuroic acid and neosidomycin
Giguere, Denis,Martel, Julien,Shiao, Tze Chieh,Roy, Rene
scheme or table, p. 9687 - 9698 (2012/01/03)
The de novo synthesis of carbohydrates constitutes an important aspect of organic chemistry, and its application toward deoxy sugars is particularly noteworthy in targeting biologically active compounds. The enantioselective preparation of 4-deoxy-d-ribo-, 4-deoxy-d-lyxo-, and 4-deoxy-d-xylo- hexopyranosides, along with their uronate counterparts has been successfully accomplished using hetero-Diels - Alder reactions as the key step. Jacobsen chromium(III) catalyst and a titanium - binaphthol complex have been used to successfully catalyze diene and aldehyde cycloadditions, leading to optically active dihydropyran templates. 6-Hydroxydesosamine, orthogonally protected ezoaminuroic acid, and neosidomycin were synthesized using a comparative study. Also, a novel chiron approach to 4-deoxy-lyxo-hexopyranosiduronic acid methyl ester derivatives was efficiently accomplished starting from readily accessible starting materials. This work represents a systematic and comprehensive study toward a de novo synthesis of 4-deoxy-hexopyranoses via enantioselective hetero-Diels-Alder reactions.
SYNTHESIS OF METHYL ETHERS OF URONIC ACIDS. III. SYNTHESIS OF METHYL (METHYL-α-D-MANNOPYRANOSID)URONATE AND ITS 2- AND 4-O-METHYL ETHERS
Grishkovets, V. I.,Zemlyakov, A. E.,Chirva, V. Ya.
, p. 401 - 403 (2007/10/02)
The synthesis of methyl (methyl α-D-mannopyranosid)uronate and its 2- and 4-O-methyl ethers has been effected by the chromium trioxide oxidation of the corredponding O-benzyl and O-benzylidene derivatives of methyl α-D-mannopyranoside, esterification with
METHANOLYSIS STUDIES OF CARBOHYDRATES, USING H.P.L.C.
Cheetham, Norman W. H.,Sirimanne, Padmini
, p. 1 - 10 (2007/10/02)
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.
