Quantitative Estimation of the Fehling Reaction of 1-<I>O</I>-Protected Uronic Acids
スポンサーリンク
概要
- 論文の詳細を見る
Quantitative estimation of the Fehling reaction of 1-<I>O</I>-protected uronic acid derivatives showed that the reducing power of 1-<I>O</I>-protected hexofuranuronic acid derivatives corresponds to 23–37% of that of D-glucose. The presumption that the reducing ability might be attributed to the formation of unsaturated <I>aldehydo</I>-sugars by removal of the 1-<I>O</I>-protecting group through a cupric ion-catalyzed β-elimination was supported by the fact that 2,5-dimethoxy-6-oxo-2,4-hexadienoic acid was formed by alkaline β-elimination of methyl (methyl 2,3,5-tri- <I>O</I>-methyl-α-D-glucofuranosid)uronate.
- 公益社団法人 日本化学会の論文
著者
-
Yoshimura Juji
Laboratorium für Organische Chemie Technische Hochschule Tokyo
-
Hashimoto Jun-ichi
Laboratory of Chemistry for Natural Products, Faculty of Science, Tokyo Institute of Technology
-
Ando Hiroaki
Laboratory of Chemistry for Natural Products, Faculty of Science, Tokyo Institute of Technology
関連論文
- Branched-chain Sugars. XVII. Stereoselectivity in the Oxidation of Several Methyl 4,6-O-Benzylidene-2-C- or -3-C-methylene-α- and-β-D-hexopyranosides with m-Chloroperbenzoic Acid
- Branched-Chain Sugars. I. On the Configuration of Branched-Chain Derivatives of 1,2 : 5,6-Di-O-isopropylidene-α-D-ribo-hexofuranos-3-ulose
- Branched-chain Sugars. VIII. On the Configuration of Branched-chain Sugars from Methyl 3-O-Benzoyl-4,6-O-benzylidene-α-D-arabino-hexopyranosid-2-ulose
- Studien über D-Glucosamin-derivaten. VII. Darstellung von 3, 4; 5, 6-Di-O-isopropyliden-N-acetyl-D-glucosaminsäure über das entsprechende D-Glucosaminol-derivat
- Branched-chain Sugars. VI. Reaction of Methylene Dimagnesium Bromide with Uloses
- Aminosugars. XXVIII. A Facile Synthesis of Benzyl α- and β-Kasugaminides via the Corresponding Abequosides
- Branched-chain Sugars. XXXV. The Synthesis of L-Rubranitrose (2,3,6-trideoxy-3-C-methyl-4-O-methyl-3-nitro-L-xylo-hexopyranose)
- Synthesis of 4-(D-alanylamino)-2-amino-2,4-dideoxy-D-xylose.
- The synthesis and reaction of spiro(oxolane-2,2'-piperazine)-3',6'-diones with N-bromosuccinimide in the presence or absence of water.
- Branched-chain sugars. XXII. Synthesis of benzyl 2,3-di-O-benzyl- and 2,3-O-methylene-.BETA.-L-threo-pentopyranosid-4-uloses, and the corresponding 6-deoxy-.ALPHA.-D-xylo-hexopyranosid-4-uloses.
- .ALPHA.,.BETA.-Unsaturated carboxylic acid derivatives. XIII. The synthesis and configuration of alkyl 2-acylamino-2-alkenoates and their cyclized 2,5-piperazinedione derivatives.
- Branched-chain sugars. XXVIII. Synthesis of 2-C-methyl-L-glyceraldehyde, 2-C-methyl-D-erythrose, and 3-C-methyl-L-erythrose derivatives.
- Quantitative Estimation of the Fehling Reaction of 1-O-Protected Uronic Acids
- Syntheses of N-Substituted Carbamimidoylformic Acids
- Aminosugars. XXVI. Synthesis of amido-bonded disaccharides containing hexosaminuronic acids.
- Dehydrooligopeptides. III. Synthesis of (Z,Z)- and (Z,E)-geometric isomers of dehydrodipeptides and their base-catalyzed transformation to the hydantoin derivatives.
- The confirmation of the configuration of ethyl 2-bromo-3-nitro-2-alkenoate by 13C NMR spectroscopy.
- Asymmetric Reactions. VI. Asymmetric Hydrogenation of Atropate Catalyzed by Cyanocobalt-Opticall Active Diamine Complex
- Asymmetric Reactions. V. Homogeneous Hydrogenation of Unsaturated Compounds Catalyzed by Bis(dimethylglyoximato)cobalt(II)
- Preparations and properties of optically active (alkyl)bis(dimethylglyoximato)cobalt(III) complexes.
- Asymmetric Hydrogenation Catalyzed by Bis(dimethylglyoximato)cobalt(II)-Optically Active Amine Complex
- .ALPHA.,.BETA.-Unsaturated carboxylic acid derivatives. XVII. The facile synthesis of ethyl .ALPHA.-azido-.ALPHA.-alkenoates and reduction to ethyl .ALPHA.-amino-.ALPHA.-alkenoates.
- .ALPHA.,.BETA.-Unsaturated carboxylic acid derivatives. XIV. The synthesis and reduction of Diels-Alder adducts from ethyl 3-nitro-2-alkenoates and cyclopentadiene.
- .ALPHA.,.BETA.-Unsaturated carboxylic acid derivatives. XV. The reaction of ethyl 3-nitro-2-alkenoate with bromine azide or bromine, and transformations of the products.
- .ALPHA.,.BETA.-Unsaturated carboxylic acid derivatives. XXI. A novel synthesis of .ALPHA.-dehydroamino acid derivatives by the Arbusov reaction of .ALPHA.-phosphoranylideneamino-2-alkenoates.
- Dehydrooligopeptides. II. The synthesis of dehydrodehydrodipeptides by direct coupling and base-catalyzed .BETA.-elimination.
- A Novel Synthesis of Ethyl β-Diethoxyphosphinyl-α,β-unsaturated-carboxylates
- The formation of the main skelton of bicyclomycin by the cyclization of 6-hydroxy-3-(3-hydroxypropyl)-2,5-piperazinedione derivatives.
- Branched-chain sugars. V. Stereoselective synthesis of 3-C- and 5-C-methyl-D-glucoses, and 5-C-methyl-L-idose derivatives.
- .ALPHA.,.BETA.-Unsaturated carboxylic acid derivatives. XIX. The convenient synthesis of .ALPHA.-alkoxy-, .ALPHA.-hydroxy-.ALPHA.-amino acid, and its cyclic dipeptide from .ALPHA.-dehydroamino acid.
- A convenient synthesis of 6-hydroxy-7,9-bis(p-methoxybenzyl)-5-methylene-2-oxa-7,9-diazabicyclo(4.2.2)decane-8,10-dione.
- Aminosugars. XXXI. Preparation of benzyl 2-acylamino-4-azido-2,4-dideoxy-ribo- and -lyxopyranosides by inversion of hydroxyl group on C-3.
- Aminosugars. XXIII. L-Idofuranose Derivatives Containing a Heterocycle at C-5,6 Position
- Oxidative removal of N-(4-methoxybenzyl) group on 2,5-piperazinediones with cerium(IV) diammonium nitrate.
- Branched-chain sugars. XXI. Synthesis of new branched-chain cyclitols having neo-, myo-, and chiro-configurations from 3-O-benzyl-5,6-dideoxy-5-C-(1,3-DITHIAN-2-YL)-6-NITRO-D-galactofuranose and -L-altrofuranose.
- Amino sugars. XXXII. Ammonolysis and azidolysis of benzyl 2,3-anhydro-4-azido-4-deoxypentopyranosides.
- Branched-chain Sugars. III. Addition of Vinylmagnesium Bromide to 5,6-Dideoxy-1,2-O-isopropylidene-6-C-nitro-3-O-substituted-α-D-xylo-hex-5-enof uranoses
- Aminosugars. XXII. Syntheses and Properties of 6-Deoxy-6-and 3-Deoxy-3-guanidino-D-hexoses
- .ALPHA.,.BETA.-Unsaturated carboxylic acid derivatives. XII. A convenient synthesis of oxazole-4-carboxylic and 3,3-dibromo-2,2-diamino acids.
- Branched-chain Sugars. IV. Synthesis of 5,6-Dideoxy-5-C-hydroxymethyl-1,2-O-isopropylidene-6-C-nitro-3-O-substituted-α-D-glucose Derivatives
- The Reaction of β-Nitroalcohols and Reactive Aldehydes
- An Attempted Synthesis of 3,6-Epidithio-2,5-piperazinedione by Cyclization of N,N′-dialkyl-2,2′-dithiodicinnamamide
- α,β-Unsaturated Carboxylic Acid Derivatives. VIII. The Synthesis and Reaction of Esters N-Acyl-N-bromo-α-dehydroamino Acid
- Branched-Chain Sugars. II. On the Configuration of Branched-Chain Sugars from Methyl 2-O-Benzoyl-4,6-O-benzylidene-α-D-ribo-hexopyranosid-3-ulose
- α,β-Unsaturated Carboxylic Acid Derivatives. IX. The Cyclization of α-(N-Acyl-hydroxyamino) Acid Esters with Ammonia or Hydroxylamine
- .ALPHA.,.BETA.-Unsaturated carboxylic acid derivatives. XVI. Synthesis and configuration of Diels-Alder adducts from ethyl 3-nitro-2-alkenoate and 1,3-butadiene.
- Asymmetric reactions. X. Asymmetric hydrogenation catalyzed by bis(dimethylglyoximato)cobalt(II)-chiral cocatalyst (amino alcohol) system.
- α,β-Unsaturated Carboxylic Acid Derivatives. VI. New Synthesis of N-Acyl-α-dehydroamino Acid Esters
- α,β-Unsaturated Carboxylic Acid Derivatives. X. The Synthesis and Reaction of α-Azido-diethoxyphosphinyl-α- and β-alkenes
- Studies on Nitro Carboxylic Acids. III. The Reaction of α-Nitroolefins with Triethyl or Diethyl Phosphite
- Branched-chain sugars. XXXIV. Synthesis of methyl dihydroeurekanate.
- .ALPHA.,.BETA.-Unsaturated carboxylic acid derivatives. XI. Convenient synthesis of tert-butyl 2-alkoxy- and hydroxy-2-acetylamino-3-mono- or 3,3-dihaloalkanoates.
- Asymmetric Reactions. IV. An Attempted Asymmetric Reduction by a Solution of [Co(CN)5]3− and Optically Active α-Amino Acid, and Its Reactive Species
- A facile synthesis of 3-(1-benzyloxymethyl-3-hydroxypropyl)-2,5-piperazinedione.
- Synthetic studies on glycocinnamoylspermidine. II Synthesis of 4-O-(2-azido-2-deoxy-D-xylopyranosyl)-2-azido-2-deoxy-D-xylopyranose derivatives.
- Branched-chain sugars. XI. Synthesis of 2,3,6-trideoxy-3-C,4-O-dimethyl-3-nitro-D-arabino-hexopyranose (D-Evernitrose).