Branched-Chain Sugars. II. On the Configuration of Branched-Chain Sugars from Methyl 2-<I>O</I>-Benzoyl-4,6-<I>O</I>-benzylidene-α-D-ribo-hexopyranosid-3-ulose

スポンサーリンク

概要

• 論文の詳細を見る

• Stereoselectivities in diazomethane and nitromethane reaction of methyl 2-<I>O</I>-benzoyl-4,6-<I>O</I>-benzylidene-α-D-ribo-hexopyranosid-3-ulose were examined. Reduction of the epoxidation product (<B>2</B>) gave an epimeric 3-<I>C</I>-methyl derivative in contrast with that obtained by the Grignard reaction. Comparison of NMR spectra of the corresponding di-<I>O</I>-acetate of the both epimers proved that <B>2</B> has the gluco-configuration. Ring-opening of the epoxide with alkali, methanolic ammonia, and acid gave the corresponding 3-<I>C</I>-hydroxymethyl, 3-<I>C</I>-aminomethyl (<B>17</B>), and de-<I>O</I>-benzylidenated product, respectively. Hydrogenation of the 3-<I>C</I>-nitromethyl derivative (<B>21</B>) obtained by nitromethane condensation, in the presence of Raney nickel, accompanied with benzoyl-migration to give 3-<I>C</I>-benzamidomethyl derivative (<B>22</B>). De-benzoylation of <B>22</B> with methanolic potassium hydroxide gave 3-<I>C</I>-aminomethyl derivative (<B>26</B>) and an orthoester-type compound. Comparison of <B>26</B> with <B>17</B> and their derivatives indicated that <B>21</B> has the allo-configuration. The both configurations were also supported by the optical rotation of 3-<I>C</I>-benzamidomethyl derivatives in cuprammonium solution.

• 公益社団法人 日本化学会の論文

著者

• Kobayashi Kazuhiko

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

• Yoshimura Juji

  Laboratorium für Organische Chemie Technische Hochschule Tokyo

• Sato Ken-ichi

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

• SHIN Chung-gi

  Laboratory of Organic Chemistry, Kanagawa University

• Shin Chung-gi

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

関連論文

• Hydrogen peroxide induces Src family tyrosine kinase-dependent activation of Xenopus eggs
• Total Synthesis of a Macrocyclic Antibiotic, Micrococcin P_1
• Total Synthesis of a Macrocyclic Antibiotic, Micrococcin P
• Convenient Synthesis of the Central 3,6-Di(2-thiazolyl)-2-(4-thiazolyl)-pyridine Skeleton of a Macrocyclic Antibiotic, GE 2270 A
• Synthesis of a Fragment A Derivative of an Antibiotic, Nosiheptide
• Total Synthesis of Antibiotic, Micrococcin P, from 2, 3, 6-Polythiazolesubstituted Pyridine Skeleton[Fragment A-C]
• Synthesis of the Central Heterocyclic Skeleton of an Antibiotic, A10255
• Useful Synthesis of 2, 3, 6-Polythiazolesubstituted Pyridine Skeleton [Fragment A-C]of Peptide Antibiotic, Micrococcin P
• Dehydrooligopeptides. XIV. Syntheses of 2-[(Z)-1-Amino-1-alken-1-yl]oxazole-4-carboxylic Acid and the Main Common Skeleton of Thiostrepton Peptide Antibiotics, A10255G and J^
• Syntheses of 2-[(1S,3S)-1-Amino-3-carboxy-3-hydroxypropyl]-thiazole-4-carboxylic Acid and the Tripeptide Skeleton of Nosiheptide Containing the Acid
• Dehydrooligopeptides. XVII. Practical Syntheses of All of the Diastereomers of N,N-Protected 2,3-Diaminobutanoic Acids from L-and D-Threonine Derivatives
• Convenient Syntheses of Thiazoles Incorporated with α-Dehydroamino Acid and Dehydropeptide Structures
• Crystal Structure of(1R, 2R, 3S, 4S, 5S, 6S, 7R, 9S)-6-Azido-7-cyano-3-C-hydroxy-methyl-3, 3'-di-O-isopropylidene-9-methoxy-2, 4, 5-tris(O-methoxymethyl)-2, 3, 4, 5-tetrahydroxy-8-oxabicyclo[4. 3. 0]nonane, toward Tetrodotoxin
• Total Synthesis of Bistratamides G and H from Various Kinds of ΔAla and ΔAbu-Containing Oligopeptides
• Convenient Syntheses of 3-Deoxy-D-manno-2-octulosonic Acid (KDO) and 3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid (KDN) Derivatives from D-Mannose
• Convenient Synthesis of the Main Dehydrohexapeptide Skeleton Constituting a Macrocyclic Antibiotic, Berninamycin A
• Total Syntheses of Bistratamides J, E, and H from Two Types of ΔAla-Containing Oligopeptides
• Useful Intermediates, 3-C-Dichloromethyl Furanose Derivatives, for the Synthesis of Branched-Chain Functionalized Sugars
• Novel Synthesis of the Main Central 2,3,6-Trisubstituted Pyridine Skeleton [Fragment A-B-C] of a Macrobicyclic Antibiotic, Cyclothiazomycin
• Convenient Synthesis of a Central 2,3,6-Trisubstituted Pyridine Skeleton of a Macrobicyclic Antibiotic, Cyclothiazomycin
• Useful Synthesis of Fragment A-C-D of a Thiostrepton-type Macrocyclic Antibiotic, Thiocilline I
• Asymmetric Synthesis of the Main Pyridine Skeleton for a Macrobicyclic Antibiotic, Cyclothiazomycin
• Dehydrooligopeptides. XX. Unusual Peptide Bond Cleavage of Dehydrotripeptide Esters Containing α-Dehydroamino Acid Residue at P_2 by Using Papain
• Dehydrooligopeptides. XVIII. Enzymatic Hydrolysis and Coupling of Dehydrodipeptide Esters Containing α-Dehydroamino Acid Residue by Using Papain
• Convenient Synthesis of Dehydrooligopeptides Containing α-Dehydroamino Acid Residue Alone
• Crystal Structure of Potential Key Compounds, DL-(1, 2, 3', 4, 5, 6'/3, 6)-6-Azido-5'-O-t-butyldiphenylsilyl-6-(cyano)hydroxymethyl-3, 5-di-C-hydroxymethyl-1, 2 : 3, 3'-di-O-isopropylidene-4-O-methoxymethyl-1, 2, 3, 4-cyclohexanetetrol, toward(±)-Tetrodot
• An Efficient Deoxysugar Synthesis using Bu4NBH4 via an SN2 Reduction
• Total Synthesis of a Novel β-Glucosidase Inhibitor, Cyclophellitol Starting from D-Glucose
• Reaction of α-Hydroxydichloromethyl Derivatives with Cesium Acetate
• A Novel Method for Constructions of β-D-Mannosidic, 2-Acetamido-2-deoxy-β-D-mannosidic, and 2-Deoxy-β-D-arabino-hexopyranosidic Units from the Bis(triflate) Derivative of β-D-Galactoside
• A Novel Method for Constructing β-D-Mannosidic, 2-Acetamido-2-deoxy-β-D-mannosidic, and 2-Deoxy-D-arabino-hexopyranosidic Units from the Bis(triflate) Derivative of β-D-Galactoside
• 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. XXIX. Synthesis of Moenuronic Acid (4-C-Methyl-D-glucuronic Acid)
• Branched-chain Sugars. IX. Reaction of 3,6-Anhydro-1,2-O-isopropylidene-α-D-ribo-hexofuranos-3-ulose with Nitromethane or Hydrogen Cyanide
• 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. XXIII. Stereoselectivities in the Addition of Nucleophiles to Several 4-Uloses
• Branched-chain Sugars. VI. Reaction of Methylene Dimagnesium Bromide with Uloses
• Branched-chain Sugars. XX. Kinetic Studies on the Epimerization of 1,2 : 5,6-Di-O-isopropylidene-3-C-nitromethyl-α-D-allofuranose
• α,β-Unsaturated Carboxylic Acid Derivatives. IV. General Synthesis of Unsaturated Unsymmetric 3,6-Disubstituted-2,5-piperazinediones
• Aminosugars. XXVIII. A Facile Synthesis of Benzyl α- and β-Kasugaminides via the Corresponding Abequosides
• Branched-chain Sugars. XII. The Stereoselectivities in the Reaction of Methyl 4,6-O-Benzylidene-α- and -β-D-hexopyranosid-3-uloses with Diazomethane
• Synthesis of 2,2-Di-C-methyl-2-deoxy- and 4,4-Di-C-methyl-4-deoxypyranosides via Michael Addition of Conjugated Enopyranosiduloses
• 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.
• Branched-chain Sugars. XIX. On the Application of 13C NMR Spectroscopy to the Configurational Assignment of 3-C-Substituents of Aldohexopyranose Derivatives
• The synthesis and reaction of spiro(oxolane-2,2'-piperazine)-3',6'-diones with N-bromosuccinimide in the presence or absence of water.
• Synthesis of (3Z, 6E)-1-N-Methylalbonoursin, a New Metabolite from Streptomyces albus
• 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. IX. Syntheses and conversions of .ALPHA.-dehydroglutamine derivatives to N-carboxy-.ALPHA.-dehydroglutamine anhydride and .DELTA.1-dehydroglutaminyldipeptides.
• 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.
• The Synthesis and Reaction of α,β-Unsaturated α-Nitrocarboxylic Esters
• .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.
• The Independent Isolation of a Primary Enamine and the Tautomeric Imine
• Branched-chain sugars. XI. Synthesis of 2,3,6-trideoxy-3-C,4-O-dimethyl-3-nitro-D-arabino-hexopyranose (D-Evernitrose).
• Convenient synthesis of 3-aminocoumarin derivatives by the condensation of 1,4-diacetyl-or 3-substituent-2,5-piperazinediones with various salicylaldehyde derivatives.

もっと見る 閉じる

スポンサーリンク