Stereoselective Glycosylation of Thioglycosides Promoted by Respective Combinations of N-Iodo-or N-Bromosuccinimide and Trityl Tetrakis(pentafluorophenyl)borate.Application to One-Pot Sequential Synthesis of Trisaccharide

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概要

• 論文の詳細を見る
• 2000-02-05

著者

• TAMURA Takayuki

  Department of High Energy Astrophysics, Institute of Space and Astronautical Science (ISAS), Japan A

• MUKAIYAMA Teruaki

  Department of Applied Chemistry, Faculty of Science, Science University of Tokyo (SUT)

• Mukaiyama Teruaki

  Department Of Applied Chemistry Faculty Of Science Science University Of Tokyo

• Takeuchi K

  Department Of Applied Chemistry Faculty Of Science Science University Of Tokyo

• Tamura Takashi

  Department Of Applied Chemistry Faculty Of Science Science University Of Tokyo

• TAKEUCHI Kazuya

  Department of Applied Chemistry, Faculty of Science, Science University of Tokyo

• Tamura Takayuki

  Department Of Applied Chemistry Faculty Of Science Science University Of Tokyo

• Takeuchi Kazuya

  Department Of Applied Chemistry Faculty Of Science Science University Of Tokyo

• Tamura T

  Department Of Applied Chemistry Faculty Of Science Science University Of Tokyo

関連論文

• The X-Ray Observatory Suzaku
• Hard X-ray Detector (HXD) on board Suzaku
• In-Orbit Performance of the Gas Imaging Spectrometer onboard ASCA
• Uniformity in the Temperature and Metallicity of the X-Ray Emitting Gas in the Abell 1060 Cluster of Galaxies
• A Catalytic Asymmetric Michael Reaction of Silyl Enol Ethers with α,β-Unsaturated Ketones Using a Chiral Titanium Oxide
• Stereoselective Synthesis of 1,2-cis-Arabinofuranosides Using a Titanium Catalyst
• ASCA Measurements of Silicon and Iron Abundances in the Intracluster Medium
• ASCA Observation of the Poor Cluster of Galaxies AWM 7 : Evidence of an Abundance Increase in the Intra-Cluster Medium at the Center
• X-Ray Temperature and Mass Measurements to the Virial Radius of Abell 1413 with Suzaku
• Asymmetric Allylation of Carbonyl Compounds with Tartrate-Modified Chiral Allylic Tin Reagents
• Asymmetric Allylation of Aromatic Aldehydes Using Chiral Allylic Tin Reagents
• An Asymmetric Synthesis of the ABC Ring System of 8-Demethyltaxoids from Optically Active 8-Membered Ring Compound via Intramolecular Aldol and Pinacol Coupling Reactions
• An Asymmetric Synthesis of the BC Ring System of 8-Epitaxoids by Way of Intramolecular Aldol and Successive Stereoselective Methylation Reactions
• An Asymmetric Synthesis of the Fully Functionalized AB Ring System of 12-Demethyltaxol via Successive Stereoselective Allylation and Intramolecular Aldol Reactions
• New Synthesis of Pinacols By Oxidative Coupling Mediated by 1,2-Dusulfides as Dehydrogenating Reagents under Irradiation
• Magnesium Bromide Diethyl Etherate Mediated Highly Diastereoselective Aldol Reaction between an Aldehyde and a Silyl Enol Ether
• Aldol Reaction of Enol Esters Catalyzed by Cationic Species Paired with Tetrakis(pentafluorophenyl)borate
• A New and Efficient Method for Oxidation of Various Alcohols by Using N-tert-Butyl Phenylsulfinimidoyl Chloride
• A Novel Carbocationic Species Paired with Tetrakis(pentafluorophenyl)Borate Anion in Catalytic Aldol Reaction
• PREPARATION OF USEFUL SYNTHETIC INTERMEDIATES OF TAXOL ANALOGS, CYCLOOCTENONE DERIVATIVES
• Construction of AB-Ring System of Taxane Framework by A-Ring Annulation Strategy : Synthesis of 1-Hydroxy-8,11,11-trimethylbicyclo-[5.3.1]undec-7-en-9-one by Way of Intramolecular Aldol Cyclization to Form the C1-C10 Bond
• A New Method for the Synthesis of Unsymmetrical Bis-Aldols by the Samarium(II) Iodide-Mediated Aldol Reaction of Aldehydes with Aryl or Alkyl Oxiranyl Ketones
• Synthesis of 18-Demethyltaxoid via Stereoselective Allylation and Intramolecular Aldol Condensation Reactions
• A New and Convenient Method for the Preparation of Cyclooctanone Containing Bis-Aldol Skelton by Samarium(II) Iodide-mediated Intramolecular Aldol Cyclization of ω-Oxiranyl Keto Octanal
• A Synthesis of AB-Ring Model System of Taxane Framework by Way of Intramolecular Knoevenagel Cyclization
• A Novel Activating Agents of 'Disarmed' Thioglycosides, Combination of Trityl Tetrakis(pentafluorophenyl)borate, Iodine and 2,3-Dichloro-5,6-dicyano-p-benzoquinone (DDQ)
• Stereoselective Glycosylation of Thioglycosides Promoted by Respective Combinations of N-Iodo-or N-Bromosuccinimide and Trityl Tetrakis(pentafluorophenyl)borate.Application to One-Pot Sequential Synthesis of Trisaccharide
• The Trityl Tetrakis(pentafluorophenyl)borate Catalyzed Stereoselective Glycosylation Using New Glycosyldonor, 3, 4,, 6-Tri-O-benzyl-2-O-p-toluoyl-β-D-glucopyranosyl Phenylcarbonate
• A Useful Method for the Preparation of Carboxylic Esters from Free Carboxylic Acids and Alcohols
• A Convenient Synthesis of Carboxanilides from Silyl Carboxylates and Weakly Nucleophilic Anilines Using p-Trifluoromethylbenzoic Anhydride and a Catalytic Amount of Active Titanium (IV) Salt
• Facile Synthesis of Lactones from Silyl ω-Siloxycarboxylates Using p-Trifluoromethylbenzoic Anhydride and a Catalytic Amount of Active Lewis Acid
• A New and Efficient Method for the Preparation of S-Phenyl Carbothioates via Mixed Anhydrides Using Active Titanium(IV) Salts
• An Efficient Method for the Preparation of Carboxylic Esters via Mixed Anhydrides by the Promotion of a Catalytic Amount of Lewis Acid
• The Catalytic Diels-Alder Reaction Using Combined Catalyst System of Diphenyltin Sulfide or Lawesson's Reagent and Silver Perchlorate
• An Asymmetric Synthesis of Fully Functionalized B Ring System of Taxol
• The Esterification Reaction between Silyl Derivatives of Carboxylic Acids and Alcohols by the Promotion of a Catalytic Amount of Lewis Acid
• Catalytic and Stereoselective Glycosylation with a Novel and Efficient Disarmed Glycosyl Donor : Glycosyl p-Trifluoromethylbenzylthio-p-trifluoromethylphenyl Formimidate
• Synthesis of Vicinal Bis(alkylthio) Derivatives by Reductive Coupling of Dithioacetals Derived from Aromatic Aldehydes with Low Valent Titanium Iodide Species
• A New Method for the Synthesis of Baccatin III
• Stereocontrolled Synthesis of the BC Ring System of Taxol
• Determination of Relative and Absolute Stereochemistry of Cephalosporolide D and Its Enantioselective Total Synthesis
• Enantioselective Borohydride Reduction of N-Diphenylphosphinyl Imines Using Optically Active Cobalt(II) Complex Catalysts
• Practical and Efficient Enantioselective Borohydride Reduction of Aromatic Ketones Catalyzed by Optically Active Cobalt(II)Complexes Using Pre-Modified Borohydride
• Enantioselective Borohydride Reduction of Ketones Catalyzed by Optically Active Cobalt(II)Complexes : Achievement of High Enantioselection by Modified Borohydrides with Furfuryl Alcohol Derivatives
• Convenient Method for One-pot Perparation of 1, 2-Diamines form Nitroolefins
• Stereoselective Synthesis of N-Acetyl-α-neuraminosyl-galactose Disaccharide
• A New Efficient Method for Catalytic Hydrolysis of Thioglycoside
• A Novel Catalyst System, Antimony(V) Chloride-Lithium Perchlorate(SbCl_5-LiClO_4), in the Friedel-Crafts Acylation Reaction
• Highly Stereoselective Synthesis of 1,2-trans-Glycosides Using p-Chlorobenzylated Glycosyl Carbonate as Glycosyl Donor
• Catalytic Stereoselective Synthesis of α-D-Galactopyranosides from 2, 3, 4, 6-Tetra-O-benzyl-D-galactopyranose and Several Alcoholic Nucleophiles
• Diastereoselective Aldol and Reformatsky Reactions of α-Halo Carbonyl Compounds and Aldehydes Mediated by Titanium(II) Chloride
• Efficient Diastereoselective Pinacol Reaction of Aliphatic and Aromatic Aldehydes by Combined Use of Newly Utilized Titanium (II) Bromide and Copper
• A Direct and Selective Syntheses of α, α-Dichloro-and α-Chloro-ethyl Ketones by the Reaction of Alkyl Carboxylates with 1, 1-Dichloroethyllithium
• Diastereoselective Aldol Reaction of α-Bromo Ketones with Aliphatic Aldehydes by Using Titanium(II) Chloride and Copper
• Efficient Method for Pinacol Coupling of Aromatic and Aliphatic Ketones by Using Titanium (II) Chloride and Zinc in the Presence of Pivalonitrile
• Efficient Method for the Preparation of Aromatic Bromides and Iodides by Ferrocenium Tetrakis[3,5-bis(trifluoromethyl)phenyl]borate-Catalyzed Halogenation with Bromine and Iodine Monochloride
• Oxidative Deamination of Various Primary Amines to the Corresponding Carbonyl Compounds by Using N-tert-Butylphenylsulfinimidoyl Chloride
• Oxidation of Various Secondary Amines to Imines with N-tert-Butylphenylsulfinimidoyl Chloride
• A Significant Effect of a Lithium Salt in the Stereocontrolled Synthesis of α-D-Ribofuranosides
• Trityl Salt Catalyzed Stereoselective Glycosylation of Alcohols with 1-Hydroxyribofuranose
• A Convenient Method for the Preparation of Unsymmetrical Bis-Aldols by Way of Sequential Two Aldol Reactions
• A Convenient Method for the Preparation of Nitro Olefins by Nitration of Olefins with Nitrogen Monoxide
• Enantioselective Aerobic Oxidation of Sulfides Catalyzed by Optically Active β-Oxo Aldiminatomanganese(III) Complexes
• An Effective Method for the Preparation of Chiral Polyoxy 8-Membered Ring Enone Corresponding to the B Ring of Taxol
• An Effective Method for the Preparation of Optically Active Polyoxy 8-Membered Ring Enone Corresponding to the B Ring of Taxol
• Diastereoselsctive Pinacol Coupling Reaction of Alipatic and Aromatic Aldehydes Promoted by Low Valent Titanium Iodide in situ Formed by Titanium(IV) Iodide and Copper
• Highly Stereoselective Preparation of α-Glucosides Utilizing Anomerization Reaction with MgBr_2-OEt_2 and a Catalytic Amount of Titanium(IV)tetrahalides
• An Efficient Method for Catalytic Stereoselective Synthesis of α-L-Fucopyranosides
• A New Efficient Method for Stereoselective Synthesis of 2-Deoxy-C-ribofuranosides
• Catalytic Stereoselective Synthesis of Pyrimidine 2-Deoxyribonucleosides
• The Catalytic Friedel-Crafts Acylation Reaction of Aromatic Compounds with Carboxylic Anhydrides Using Combined Catalyst System of Titanium(IV)Chloride Tris(trifluoromethanesulfonate)and Trifluoromethanesulfonic Acid
• New and Efficient Method for the Preparation of Medium-sized Lactones from the Correspondingω-Hydroxycarboxylic Acids
• An Efficient Esterification Reaction between Equimolar Amounts of Free Carboxylic Acids and Alcohols by the Combined Use of Octamethylcyclotetrasiloxane and a Catalytic Amount of Titanium(IV) Chloride Tris(trifluoromethanesulfonate)
• A Convergent Total Synthesis of the Mucin Related F1α Antigen by One-Pot Sequential Stereoselective Glycosylation
• Trityl Tetrakis(pentafluorophenyl)borate Catalyzed Stereoselective Glycosylation Using Glycopyranosyl Fluoride as a Glycosyl Donor
• Highly α-Selective Glycosylation with Glycopyranosyl Fluorides Having Diethylthiocarbamoyl Group
• An Efficient Method for Catalytic and Stereoselective Glycosylation with Thioglycosides Promoted by Trityl Tetrakis (pentafluorophenyl) borate and Sodium Periodate
• A New Method for Oxidation of Various Alcohols to the Corresponding Carbonyl Compounds by Using N-t-Butylbenzenesulfinimidoyl Chloride
• Polymer-supported Sulfinimidoyl Chloride as a Useful Reagent for Oxidation of Various Alcohols to the Corresponding Carbonyl Compounds
• Catalytic Oxidation of Various Alcohols to the Corresponding Carbonyl Compounds with N-Chlorosuccinimide Using a Catalytic Amount of Sulfenamide
• Oxidation of Primary Alkyl Triflates to the Corresponding Aldehydes via Alkoxy(N-tert-butylamino)(methyl)sulfonium Triflates
• An Efficient Method for the p-Methoxybenzylation of Hydroxy Groups with 2-(4-Methoxybenzyloxy)-3-nitropyridine
• A Mild and Efficient Oxidation of Alcohols with N-tert-Butylphenylsufinimidoyl Chloride in the Coexistence of Zinc Oxide
• Benzylation of Alcoholic Hydroxyl Groups with Benzyl Mesylate by Using a Catalytic Amount of Lithium Tetrakis(pentafluorophenyl)borate in the Coexistence of Lithium Triflate and Magnesium Oxide
• A New and One-Pot Synthesis of α,β-Unsaturated Ketones by Dehydrogenation of Various Ketones with N-tert-Butyl Phenylsulfinimidoyl Chloride
• An Efficient Method for Catalytic and Stereoselective Synthesis of 2-Deoxy-α-D-glucopyranosides from 3, 4, 6-Tri-O-benzyl-2-deoxy-D-glucopyranose and Several Alcoholic Nucleophiles
• A Convenient Method for the Preparations of Carboxamides and Peptides by Using Di(2-pyridyl) Carbonate and O
• A Novel Method for the Synthesis of Thiols from the Corresponding Olefins by Using Thiocarbanates and Ti(IV) Halides
• Effective Activation of 'Armed' Thioglycoside with a New Combination of Trityl Tetrakis(pentafluorophenyl)borate [TrB(C_6F_5)_4] and N - (Ethylthio)phthalimide (PhthNSEt)
• Protic Acid Catalyzed Stereoselective Glycosylation Using Glycosyl Fluorides
• 1,2-Cis Selective Glycosylation with Glycosyl Fluoride by Using a Catalytic Amount of Trifluoromethanesulfonic Acid (TfOH) in the Coexistence of Molecular Sieve 5A (MS5A)
• Trifluoromethanesulfonic Acid (TfOH)-Caralyzed Stereoselective Glycosylation Using Glycosyl Fluoride
• Catalytic and Stereoselective Glycosylation with Disarmed Glycosyl Fluoride Having Phthaloyl of Dichlorophthaloyl Protected Amino Function Using a 1:2 Combination or Stannic Chloride adn Silver Tetrakis(pentafluorophenyl)borate
• A Catalytic and Stereoselective Glycosylation with Glucopyranosyl Fluoride by Using Various Protic Acids
• Catalytic and Stereoselective Glycosylation with Disarmed Glycosyl Fluoride by Using a Combination of Stannous(II) Chloride (SnCl_2 ) and Silver Tetrakis(pentafluorophenyl)borate [AgB(C_6F_5)_4] as a Catalyst
• Catalytic Stereoselective Synthesis of α- or β-Glucosides Using a Single Glycosyl Donor, 1-O-2'(2'-Methoxyethoxy)acetyl-Glucopyranose Derivative
• Synthesis of AB Ring Model System of Taxol via Allylation of 8-Membered Ring Compound and Intramolecular Aldol Condensation
• Novel Zirconium-Iron Multinuclear Complex Catalysts for Olefin Polymerizations
• Stereoselective Cyclopolymerization of 1,5-Hexadiene Using Novel Bis(ferrocenyl)zirconocene Catalyst
• Preparation of Narrow Polydispersity Polycaprolactone Catalyzed by Cationic Zirconocene Complexes

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