Branched-chain Sugars. III. Addition of Vinylmagnesium Bromide to 5,6-Dideoxy-1,2-<I>O</I>-isopropylidene-6-<I>C</I>-nitro-3-<I>O</I>-substituted-α-D-<I>xylo</I>-hex-5-enof uranoses

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概要

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• Addition of vinylmagnesium bromide to 3-<I>O</I>-acetyl (<B>1</B>) and 3-<I>O</I>-benzyl (<B>3</B>) derivatives of 5,6-dideoxy-1,2-<I>O</I>-isopropylidene-6-<I>C</I>-nitro-α-D-<I>xylo</I>-hex-5-enofuranose gave the corresponding 5-deoxy-5-<I>C</I>-vinyl derivatives of L-<I>ido</I>-type, of which the configurations were proved by intramolecular cyclization into the corresponding nitrocyclitojs. Conformations of <B>1</B> and <B>3</B> and that of the transition state in the addition reaction were discussed on the basis of their NMR parameters.

• 公益社団法人 日本化学会の論文

著者

• Funabashi Masuo

  Laboratory of Chemistry for Natural Products, Faculty of Science, Tokyo Institute of Technology

• Yoshimura Juji

  Laboratorium für Organische Chemie Technische Hochschule Tokyo

• Iida Takao

  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).

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