6-Nitro-2-benzothiazolyl α-Mannoside : A Highly Efficient Mannosyl Donor in Constructing β-Man(1→4)GlcN Linkage and Its Application to the Synthesis of the Pentasaccharide Core of N-Glycans

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概要

• 論文の詳細を見る
• Chemical Society of Japanの論文
• 2006-03-15

著者

• Mukaiyama Teruaki

  Center For Basic Res. The Kitasato Inst.

• Mandai Hiroki

  Center For Basic Research The Kitasato Institute (tci)

関連論文

• Cyanation of Alcohols with Diethyl Cyanophosphonate and 2,6-Dimethyl-1,4-benzoquinone by a New Type of Oxidation-Reduction Condensation
• Preparation of Nitriles from Primary Alcohols by a New Type of Oxidation-reduction Condensation Using 2, 6-Dimethyl-1, 4-benzoquinone and Diethyl Cyanophosphonate
• An Efficient Method for the Preparation of N-Alkylamides from Alkyl Diphenylphosphinites and Amides by Using Methyl Acrylate
• A New Method for the Preparation of Nitrogen-containing Cyclic Compounds from p-Nitrobenzenesulfonamide and Alkyl Bis(diphenylphosphinite)s by Oxidation-Reduction Condensation Using 1-Azidoadamantane
• Lewis Base-Catalyzed [2,3]-Wittig Rearrangement of Silyl Enolates Generated from α-Allyloxy Carbonyl Compounds
• The Product-catalyzed [2,3]-Wittig Rearrangement of Silyl Enolates Generated from α-Allyloxy Ketones
• Ammonium Carboxylate-catalyzed [2,3]-Witting Rearrangement of Silyl Enolates Generated from α-Allyloxy Esters
• Ammonium Phenoxides-catalyzed syn-Selective Aldol Reaction Between an Aldehyde and an Trimethylsilyl Enolate
• Lewis Base-catalyzed [2, 3]-Wittig Rearrangement of Silyl Enolates Generated from α-Allyloxy Ketones
• N-Arylation of Pyridin-2(1H)-ones with Pentavalent Organobismuth Reagents under Copper-Free Conditions
• Stereoselective Carbon-Carbon Bond Forming Reactions between Various Chiral Alkyl Aryl Carbinols and Triethyl Methanetricarboxylate by Oxidation-Reduction Condensation Using Alkyl Diphenylphosphinites
• Diastereo- and Enantioselective Tandem Michael Addition and Lactonization between Silyl Enolates and α,β-Unsaturated Ketones Catalyzed by a Chiral Quaternary Ammonium Phenoxide
• Enantioselective Synthesis of 3,4-Dihydropyran-2-ones by Chiral Quaternary Ammonium Phenoxide-catalyzed Tandem Michael Addition and Lactonization
• A Convenient Method for the Synthesis of Carboxamides and Thioesters by Using Tetrakis(2-methylimidazol-1-yl)silane
• An Efficient Method for the Preparation of Carboxamides by Dehydration Condensation Using Tetrakis(1,1,1,3,3,3-hexafluoro-2-propoxy)silane
• An Effective Method for the Synthesis of Carboxamides by Using Tetrakis(pyridine-2-yloxy)silane as a Mild Coupling Reagent
• A Convenient Method for Preparations of 1-Acylimidazoles and Carboxamides by Using Novel Imidazolylsilane Derivatives
• Stereoselective Synthesis of trans-3, 4-Dihydropyran-2-ones by Phenoxide ion-catalyzed Tandem Michael Addition and Lactonization
• An Efficient Synthesis of 3, 4-Dihydropyran-2-one Derivatives by Lewis Base-catalyzed Tandem Michael Addition and Lactonization
• Lithium Alkoxide-promoted Michael Reaction between Silyl Enolates and α, β-Unsaturated Carbonyl Compounds
• A Convenient Method for the Synthesis of (Z)-α-Fluoroacrylates : Lewis Base-catalyzed Carbonyl Fluoroolefination Using Fluoro(trimethylsilyl)ketene Ethyl Trimethylsilyl Acetal
• Copper(II)-catalyzed O-Phenylation of Alcohols with Organobismuth(V) Reagents : A Convenient Method for the Synthesis of Simple tert-Alkyl Phenyl Ethers
• New Preparative Method of Aryl Tosylates by Using Organobismuth Reagents
• Direct α-Oxytosylation of Ketones by Using Pentavalent Organobismuth Reagents
• Stereospecific C-S Bond Formation from Chiral Tertiary Alcohols by Quinone-Mediated Oxidation-Reduction Condensation Using Alkyl Diphenylphosphinites and Its Application to the Synthesis of a Chiral Tertiary Thiol
• Preparation of tert-Alkyl Aryl Sulfides from tert-Alcohols via Quinone mediated Oxidation-Reduction Condensation between tert-Alkyl Diphenylphosphinites and 2-Sulfanyl-1, 3-benzothiazole
• New methods for carbon–nitrogen, carbon–sulfur, and carbon–carbon bond formations by quinone-mediated oxidation–reduction condensation using alkyl diphenylphosphinites
• A Convenient Method for the Lewis Base-catalyzed Synthesis of α,β-Unsaturated Carboxylic Esters Using Trimethylsilylketene Ethyl Trimethylsilyl Acetal and Carbonyl Compounds
• Diastereoselective Cyanomethylation of Chiral N-(tert-Butylsulfinyl)imines Promoted by Lewis Bases
• Lewis Base Catalyzed 1,3-Dithiane Addition to Carbonyl Compounds Using 2-Trimethylsilyl-1,3-dithiane
• Trimethylsilyl Triflate Mediated New Carbon-Carbon Bond Forming Reactions between Benzyl Diphenylphosphinates and Organosilicon Compounds
• Highly Efficient Method for the Synthesis of Carboxamides from Carboxylic Acids and Amines Using Pyridine-3-sulfonyl Chloride (3-PSC)
• Highly Efficient Method for the Synthesis of Carboxamides from Carboxylic Acids and Amines Using Benzenesulfonic Anhydride (BSA)
• Pyridine-3-carboxylic Anhydride (3-PCA) : A Versatile, Practical, and Inexpensive Reagent for Condensation Reaction between Carboxylic Acids and Alcohols
• Catalytic and Stereoselective Glycosylation with Glucosyl Thioformimidates
• Efficient Method for Dehydration Condensation Using Pyridine-3-carboxylic Anhydride (3-PCA) : Synthesis of Carboxamides from Nearly Equimolar Amounts of Carboxylic Acids and Amines
• Lewis Base-catalyzed Cyanomethylation of Aldimines with Trimethylsilylacetonitrile
• Highly Stereoselective Samarium(II) Iodide-Mediated Aldol Reactions of Acylaziridines with Aldehydes
• Highly trans-Selective Synthesis of β-Lactams by Tandem Phenoxide Anion-catalyzed Mannich-type Addition and Cyclization
• Efficient Method for the Lactonization of ω-Hydroxycarboxylic Acids with Di-2-thienyl Carbonate by the Promotion of Catalytic Amounts of DMAP and Hf(OTf)_4
• Enantioselective Synthesis of C11-C17 Segment of Mycinolide IV Using Samarium(II) Iodide-mediated Aldol Reaction
• A Facile One-Pot Benzylation of Sodium Enolates Using Trifluoromethanesulfonic Anhydride and Diphenyl Sulfoxide
• Lithium Acetate-catalyzed Crossed Aldol Reaction between Aldehydes and Trimethylsilyl Enolates Generated from Other Aldehydes
• Lewis Base-catalyzed Diastereoselective Strecker-type Reaction between Trimethylsilyl Cyanide and Chiral Sulfinimines
• Lewis Base-catalyzed Diastereoselective Mannich-type Reaction between Ketene Silyl Acetals and Chiral Sulfinimines
• Lewis Base-catalyzed Trifluoromethylation of Aldimines with (Trifluoromethyl)trimethylsilane
• Stereoselective Synthesis of δ-Amino-β'-Hydroxy-β, γ-Unsaturated Esters by the Samarium(II) Iodide-mediated Aldol Reaction of Aldehydes with γ, δ-Aziridiny-α, β-Unsaturated Esters
• Conversion of Alcohols to Alkyl Aryl Sulfides by a New Type of Oxidation-Reduction Condensation Using Phenyl Diphenylphosphinite
• Stereospecific Synthesis of sec- and tert-Alkyl Azides from Alcohols and Trimethylsilyl Azide by a New Type of Oxidation-Reduction Condensation Using Phenyl Diphenylphosphinite and Trimethylsilylmethyl Azide
• Stereospecific Synthesis of Alkyl Aryl Sulfides from Alcohols and 2-Sulfanylbenzothiazole Using Aryl Diphenylphosphinite and Azide Compounds by a New Type of Oxidation-Reduction Condensation
• Preparation of Alkyl Aryl Sulfides from Alcohols and 2-Sulfanylbenzothiazole by a New Type of Oxidation-Reduction Condensation Using Aryl Diphenylphosphinite and Benzoquinone Derivatives
• Preparation of tert-Alkyl Azides from Tertiary Alcohols by Way of Benzoquinone-mediated Oxidation-Reduction Condensation
• A New Method for the Synthesis of β-Amino-β'-Hydroxy Ketones by the Samarium(II) Iodide-mediated Aldol Reaction of Aldehydes with Aryl or Alkyl Aziridinyl Ketones
• Stereoselective Synthesis of 19-Hydroxytaxoid Using Intramolecular Pinacol Coupling Reaction
• A Facile One-pot Benzylation of Sodium Enolates Using Trifluoromethansulfonic Anhydride and Diphenyl Sulfoxide
• 6-Nitro-2-benzothiazolyl α-Glucoside and α-Mannoside in β-Selective Glycosylations
• Lewis Base-Catalyzed Perfluoroalkylation of Carbonyl Compounds and Imines with (Perfluoroalkyl)trimethylsilane
• An Efficient Method for the Preparation of Chiral Mosher's Acid Analogues
• A Convenient Method for the Preparation of Alkyl Aryl Sulfides from Alcohols and (Chloromethylene)dimethylammonium Chloride
• Lewis Base-catalyzed Cyanomethylation of Carbonyl Compounds with (Trimethylsilyl)acetonitrile
• Asymmetric Trifluoromethylation of Ketones with (Trifluoromethyl)trimethylsilane Catalyzed by Chiral Quaternary Ammonium Phenoxides
• Effective Synthesis of 5-Substituted Butenolide Derivatives by Using Cinchonidine-derived Quaternary Ammonium Phenoxide Catalyst
• Efficient synthesis of substituted 3-amino-3,4-dihydropyran-2-ones diastereo and enantioselective tandem Michael addition and lactonization between α,β-unsaturated ketones and glycine-derived silyl enolates using a chiral quaternary ammonium phenoxide
• Diastereo- and Enantioselective Synthesis of 3-Amino-3,4-dihydropyran-2-ones by Tandem Michael Addition and Lactonization Using a Chiral Quaternary Ammonium Phenoxide
• Diastereo- and Enantioselective Tandem Michael Addition and Lactonization Catalyzed by Chiral Quaternary Ammonium Phenoxide : Stereoselective Synthesis of the Two Enantiomers by Using a Single Chiral Source
• A New Method for the Preparation of Alkyl Aryl Sulfides from Alcohols via Alkoxydiphenylphosphines by Oxidation-Reduction Condensation
• Convergent Total Syntheses of Oligosaccharides by One-Pot Sequential Stereoselective Glycosylations
• A Convenient Method for the Synthesis of 2-Arylaziridines from Styrene Derivatives via 2-Arylethenyl(diphenyl)sulfonium Salts
• Selective Synthesis of Isocyanides from Secondary Alcohols by a New Type of Oxidation-Reduction Condensation
• Facile One-pot Syntheses of Amidines and Enamines from Oximes via Beckmann Rearrangement Using Trifluoromethansulfonic Anhydride
• Lewis Base-catalyzed Strecker-type Reaction between Trimethylsilyl Cyanide and N-Tosylimines in Water-containing DMF
• One-pot Synthesis of β-Lactams from Aldimines and Ketene Silyl Acetals by Tandem Lewis Base-catalyzed Mannich-type Addition and Cyclization
• Efficient Method for the Esterification of Carboxylic Acids with Alcohols Using Di-2-thienyl Carbonate Promoted by Catalytic Amounts of DMAP and Hf(OTf)_4
• A New Method for the Lactonization of ω-Hydroxy Carboxylic Acids with Di-2-thienyl Carbonate by the Promotion of DMAP and Iodine
• Efficient Method for the Esterification of Carboxylic Acids with Alcohols Using Di-2-thienyl Carbonate Promoted by DMAP and Iodine
• A New Method for the Esterification of Carboxylic Acids with Various Alcohols by Using Di-2-thienyl Carbonate, a New Coupling Reagent
• Copper(II)-catalyzed O-Phenylation of Tertiary Alcohols with Organobismuth(V) Reagents
• A New Method for α-Selective Glycosylation Using a Donor, Glycosyl Methyldiphenylphosphonium Iodide, without Any Assistance of Acid Promoters
• Lewis Base-Catalyzed Michael Reactions between Trimethylsilyl Enolate and α, β-Unsaturated Carbonyl Compounds
• Lithium Acetate-catalyzed Trifluoromethylation of Carbonyl Compounds with (Trifluoromethyl)trimethylsilane
• Lewis Base-catalyzed anti-Selective Mannich-type Reaction between Trimethylsilyl Enolates and Aldimines
• Product-catalyzed Mannich-type Reaction between Trimethylsilyl Enolates and N-Tosylaldimines
• Lithium Acetate-Catalyzed Aldol Reaction between Aldehyde and Trimethylsilyl Enolate in Anhydrous or Water-Containing N, N-Dimethylformamide
• Lithium Acetate-catalyzed Michael Reaction between Trimethylsilyl Enolate and α, β-Unsaturated Carbonyl Compound
• Diastereoselective Trifluoromethylation of Chiral N-(Tolylsulfinyl)imines in the Presence of Lewis Bases
• Enantioselective Trifluoromethylation of Ketones with (Trifluoromethyl)trimethylsilane Catalyzed by Chiral Quaternary Ammonium Phenoxides
• A Versatile, Practical, and Inexpensive Reagent, Pyridine-3-carboxylic Anhydride (3-PCA), for Condensation Reactions
• Alkyl Phosphinites : Versatile Synthetic Intermediates for Dehydration Condensation Reactions
• 6-Nitro-2-benzothiazolyl α-Mannoside : A Highly Efficient Mannosyl Donor in Constructing β-Man(1→4)GlcN Linkage and Its Application to the Synthesis of the Pentasaccharide Core of N-Glycans
• Synthesis of N-Aryl Pyridin-2-ones via Ligand Coupling Reactions Using Pentavalent Organobismuth Reagents
• An Efficient Method for Alkylation of Alcohols with Alkyl P, P-diphenyl-N-(methanesulfonyl)phosphinimidates
• Efficient Method for the Preparation of Primary, Inverted Secondary and Tertiary Alkyl Carboxylates from Alcohols and Carboxylic Acids by a New Type of Oxidation-Reduction Condensation Using Simple 1,4-Benzoquinone
• Efficient Method for the Preparation of Carboxylic Acid Alkyl Esters or Alkyl Phenyl Ethers by a New-Type of Oxidation-Reduction Condensation Using 2, 6-Dimethyl-1, 4-benzoquinone and Alkoxydiphenylphosphines
• New One-pot Cross-coupling Reaction between Grignard Reagents and Alkoxymethyldiphenylphosphonium Iodides in situ-Formed from Alcohols, Chlorodiphenylphosphine and Iodomethane
• Efficient Method for the Preparation of Inverted Alkyl Carboxylates and Phenyl Carboxylates via Oxidation-Reduction Condensation Using 2, 6-Dimethyl-1, 4-benzoquinone or Simple 1, 4-Benzoquinone
• Efficient and Concise Synthesis of βMan1-4GlcN Linkage of Pentasaccharide Core by Using 6-Nitro-2-benzothiazolyl α-Mannoside
• Glycosyl Phosphonium Halide as a Reactive Intermediate in Highly α-Selective Glycosylation
• Highly α-Selective Synthesis of Disaccharide Using Glycosyl Bromide by the Promotion of Phosphine Oxide
• A Convenient Method for the Synthesis of α-Imidostyrenes from Styrenes and Imides via Diphenylstyrylsulfonium Salts
• Stereoselective Crossed Aldol Reaction via Boron Enolates Generated from α-Iodo Ketones and 9-Borabicyclo[3. 3. 1]nonane

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