Biochemical Studies on Thiosugars. IV. Synthesis of 1,6-Anhydro-1,6-sulfide-β-D-glucopyranose (Thiolevoglucosan) and 6-Deoxy-6-mercapto-1-thio-D-glucose.

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概要

• 論文の詳細を見る

• 1,6-Anhydro-1,6-sulfide-2,3,4-tri-O-acetyl-β-D-glucopyranose was synthesized by alkali-degradation and successive acetylation of 6-O-tosyl-2,3,4-tri-O-acetyl-β-D-glucopyranosyl ethylxanthate and 6-O-tosyl-1-deoxy-1-acethylthio-2,3,4-tri-O-acetyl-β-D-glucopyranose, which were prepared from 6-O-tosyl-2,3,4-tri-O-acetyl-α-D-glucopyranosyl bromide with potassium ethylxanthate and potassium thiolacetate respectively. On desulfurization of 1,6-anhydro-1,6-sulfide-2,3,4-tri-O-acetyl-β-D-glucopyranose with Raney nickel, 6-deoxy-1,5-anhydro-D-sorbitol tracetate was obtained. 1,6-Dideoxy-1,6-diacetylthio-2,3,4-tri-O-acetyl-β-D-glucopyranose was prepared from 6-deoxy-6-acetylthio-2,3,4-tri-O-acetyl-α-D-glucopyranosyl bromide, which was synthesized from 6-deoxy-6-acetylthio-1,2,3,4-tetra-O-acetyl-β-D-glucopyranose, and potassium thiolacetate. The structure was also confirmed by desulfurization with Raney nickel according to give 6-deoxy-1,5-anhydro-D-sorbitol.

• 公益社団法人日本薬学会の論文
• 1963-01-25

著者

• 赤木 満洲雄

  Faculty of Pharmaceutical Sciences, School of Medicine, Hokkaido University

• 手島 節三

  Faculty of Pharmaceutical Sciences, Nagoya City University

• 羽賀 正信

  Faculty of Pharmaceutical Sciences, School of Medicine, Hokkaido University, Nishi-5-chome, Kita-12-

• 手島 節三

  Faculty Of Pharmaceutical Sciences Nagoya City University

• 羽賀 正信

  Faculty Of Pharmaceutical Sciences Nagoya City University

• 羽賀 正信

  Faculty Of Pharmaceutical Sciences Health Sciences University Of Hokkaido

• 赤木 満洲雄

  Faculty Of Pharmaceutical Sciences Hokkaido University

関連論文

• Studies on Metabolism of 2-Methyl-3-o-tolyl-4(3H)-quinazolinone. II. Physiological Disposition and Metabolic Fate of 2-Methyl-3-o-tolyl-4 (3H)-quinazolinone.
• Studies on Metabolism of 2-Methyl-3-o-tolyl-4 (3H)-quinazolinone. I. The Estimation of 2-Methyl-3-o-tolyl-4 (3H)-quinazolinone in Biological Materials.
• Synthesis of 2-Acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-3-O-(α-L-fucopyranosyl)-D-glucopyranose (3-O-α-L-Fucopyranosyl-di-N-acetylchitobiose)
• Chemical Modification of Lactose. XIII. Synthesis of Lacto-N-tetraose
• A Preparation of the Branched Trisaccharide 2-Acetamido-2-deoxy-4-O-(β-D-galactopyranosyl)-3-O-(β-D-xylopyranosyl)-D-glucopyranose (3-O-β-D-Xylopyranosyl-N-acetyllactosamine)
• Chemical Modification of Lactose. XII. Preparation of O-(2-Acetamido-2-deoxy-β-D-glucopyranosyl)-(1→6)-O-β-D-galactopyranosyl-(1→4)-D-glucopyranose (6´-N-Acetylglucosaminyllactose)
• Synthesis of Methyl O-β-D-Galactopyranosyl-(1→6)-O-α-D-galactopyranosyl-(1→6)-O-α-D-galactopyranosyl-(1→6)-O-β-D-glucopyranoside
• Chemical Modification of Lactose. IX. Synthesis of O-β-D-Galactopyranosyl-(1→6)-O-β-D-galactopyranosyl-(1→4)-D-glucopyranose (6'-Galactosyllactose)
• A Facile Synthetic Approach for Alkyl α-Glycosides of Reducing Disaccharides
• The Lipase-Catalyzed Reaction of n-Alkyl n-Butyrates with Methanol
• Analytical Studies on Esterases using Gas-Liquid Chromatography. II. On the Alcoholytic and Hydrolytic Activities of Esterases from Swine Liver and Mucor javanicus
• Studies on Food Additives. XII. Synthesis of p-Ethoxyphenylurea N-Glucuronide, a Metabolite in Rabbit
• Studies on Food Additives. IX. Estimation of p-Ethoxyphenylurea in Biological Materials and Physiological Disposition in the Animals
• Structure of p-Ethoxyphenylurea-N-glucuronide
• Chemical Modification of Lactose. XIII. Synthesis of Lacto-N-tetraose
• New Syntheses of 6-Deoxy-L-gulose and 6-Deoxy-L-talose
• Chemical Modification of Maltose. VII. Synthesis of 4-O-(2-Acetamido-2-deoxy-α-D-glucopyranosyl)-D-glucopyranose (GlcNAcα1→4Glc)
• Chemical Modification of Maltose. VI. Selective p-Toluenesulfonylation of 1,6-Anhydro-4', 6'-O-benzylidene-β-maltose using Phase Transfer Catalysis
• Chemical Modification of Maltose. V. A New Synthesis of 2-Acetamido-2-deoxy-4-O-α-D-glucopyranosyl-α-D-glucopyranose (N-Acetylmaltosamine)
• Chemical Modification of Maltose. IV. Synthesis of 4-O-α-D-Altropyranosyl-D-glucopyranose
• Chemical Modification of Maltose. III. Selective p-Toluenesulfonylation of 1,6-Anhydro-4', 6'-O-benzylidene-β-maltose
• Studies on Catalytic Hydrogenation of the Exocyclic Double Bond in Reducing Disaccharides
• Selective Benzoylation of 1,6-Anhydro-4', 6'-O-benzylidene-β-maltose
• Syntheses of 4-O-α-D-Galactopyranosyl-D-glucopyranose and 4-O-(6-Deoxy-α-D-galactopyranosyl)-D-glucopyranose by Chemical Modifications of Maltose
• Thiosugars. XVII. Syntheses of Maltose Derivatives having Sulfur Atom in the Reducing Moiety
• キノン系化合物の抗菌性作用機序に関する研究(第1報) : キノン系化合物の化学構造と抗菌性(その1)アリルベンゾキノン類の化学構造と抗菌性
• Thiosugars. XVIII. : Synthesis of 2-Acylamino-1,6-anhydro-2,6-dideoxy-6-thio-β-D-glucopyranose
• ISOLATION OF LIMONIN AND OBACUNONE FROM PHELLODENDRI CORTEX SHORTEN THE SLEEPING TIME INDUCED IN MICE BY α-CHLORALOSE-URETHANE
• Studies on the Constitution of Edible and Medicinal Plants. I. : Isolation and Identification of 4-O-Methylpyridoxine, Toxic Principle from the Seed of Ginkgo biloba L.
• AN ANTIVITAMIN B_6,4'-METHOXYPYRIDOXINE, FROM THE SEED OF GINKGO BILOBA L.
• Thiosugars. XV. Further Contribution on Anomalous High Reactivity of Secondary Methanesulfonic Esters in Thiosugars
• Thiosugars. VI. Reaction Products of Potassium Alkyl- and Benzylxanthates with Acetylated Glucosyl Halides.
• A Novel Synthesis of Trehalose-Type Thiodisaccharides. An Anomalous Reaction of Potassium Methyl-and Benzyl-xanthates with Halogeno-O-acetyl Sugars in Acetone
• Synthesis of 2-Acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-6-O-(α-L-fucopyranosyl)-D-glucopyranose (6-O-α-L-Fucopyranosyl-di-N-acetylchitobiose)
• A New Synthesis of 2-Acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-1,3,6-tri-O-acetyl-2-deoxy-α-D-glucopyranose (Chitobiose Octaacetate)
• Syntheses of O-α-and O-β-D-Galactopyranosyl-(1→6)-O-[α-D-glucopyranosyl-(1→4)]-D-glucopyranoses
• Synthesis of O-α-and O-β-D-Galactopyranosyl-(1→6)-O-α-D-glucopyranosyl-(1→4)-D-glucopyranoses
• Chemical Modification of Lactose. V. Synthesis of 6'-Acetamido-6'-deoxy-α-lactose
• Chemical Modification of Lactose. IV. Syntheses of Disaccharide Derivatives Predominantly Modified at the C-6 Position in Lactose
• Chemical Modification of Lactose. III. Syntheses of 4'-Acetamido-4'-deoxy-α-lactose and 6'-Acetamido-6'-deoxy-α-cellobiose
• Thiosugars. XVI. Synthesis of Cellobiose Derivatives having Sulfur Atom in the Reducing Moiety
• In Vivo and in Vitro Antitumor Activity of Sugars containing Sulfur
• Studies on the Fischer's Glucal-hydrobromid-diacetat and Glucal-hydrobromid-triacetat
• Thiosugars. XIV. Studies on the Syntheses of 1,2-Dideoxy-1,2-dithioimidocarbonyl-β-D-mannopyranose and 1,2-Dideoxy-1,2-trithiocarbonyl-β-D-mannopyranose
• Thiosugars. XIII. An Attempt at Thiosugar Synthesis having a Vicinal cis-Dimercapto Group in the Pyranose Ring
• Thiosugars. XII. Studies on Unsaturated Sugars derived from Glucosyl N, N-Dimethyldithiocarbamate.
• Thiosugars. XI. Further Studies on Thiolevoglycosans.
• Studies on the Fischer's Glucal-hydrobromid-diacetat and Glucal-hydrobromid-triacetat
• Studies on Food Additives. VIII. Metabolism of α-Hydroxy-2,6-di-tert-butyl-p-cresol. Isolation of Metabolites.
• Studies on Food Additives. VI. Metabolism of 2,6-Di-tert-butyl-p-cresol (BHT) in a Rabbit. (1). Determination and Paper Chromatography of a Metabolite.
• Syntheses of Acetylated Trisaccharides, Manα1→3Manβ1→4GlcNAc and Manα1→2Manβ1→4GlcNAc, relating to Mannosidosis
• 含硫糖類の抗腫瘍性
• On the Relative Rates of Displacement Reaction of Primary p-Tosyloxy Groups of Hexapyranose Derivatives with Sodium Iodide in Acetone Solution.
• Biochemical Studies on Thiosugars. IV. Synthesis of 1,6-Anhydro-1,6-sulfide-β-D-glucopyranose (Thiolevoglucosan) and 6-Deoxy-6-mercapto-1-thio-D-glucose.
• Synthesis of Anomers of 6-O-Tosyl-1,3,4-tri-O-acetyl-N-acetyl-D-glucosamine and 1,6-Anhydro-N-acetyl-β-D-glucosamine.
• A New Synthesis of 1,6-Anhydro-β-D-glucopyranose (Levoglucosan).
• Biochemical Studies on Thiosugars. III. Synthesis of 6-Deoxy-6-mercapto-D-glucose.
• Reaction Products of Glucuronic Acid with Phenylhydrazine.
• Biochemical Studies on Thiosugars. II. Synthesis of N-Acetyl-1-thio-D-glucosamine and its Derivatives.
• Biochemical Studies on Thiosugars. I. Synthesis of 1-Thio-D-glucuronic Acid.
• Syntheses of Acetylated Tetrasaccharides, Manα1→2Manα1→3Manβ1→4GlcNAc and Manα1→3Manα1→6Manβ1→4GlcNAc
• Syntheses of 2-Acetamido-2-deoxy-4-O-β-D-galactopyranosyl-D-glucopyranose (N-Acetyllactosamine) Derivatives
• Chemical Modification of Lactose. XVII. Syntheses of O-α- and O-β-L-Fucopyranosyl-(1→4)- or -(1→6)-O-β-D-galactopyranosyl-(1→4)-D-glucopyranoses (4'- or 6'-O-α- and -O-β-L-Fucopyranosyllactoses)
• Synthesis of 2-Acetamido-1,6-anhydro-3-O-benzyl-2-deoxy-β-D-glucopyranose, a Useful Glycosyl Acceptor for 1,4-Linked, N-Acetylglucosaminecontaining Oligosaccharides Synthesis
• Chemical Modification of Lactose. XVI. : Synthesis of Lacto-N-neohexaose
• Chemical Modification of Lactose. XVI. Synthesis of Lacto-N-neohexaose
• Chemical Modification of Lactose. XI. A New Synthesis of 2-Acetamido-2-deoxy-4-O-β-D-galactopyranosyl-α-D-glucopyranose (N-Acetyllactosamine)
• Chemical Modification of Lactose. VIII. Studies on the Reactivities of the Secondary Hydroxyl Groups in 1,6-Anhydro-4', 6'-O-benzylidene-β-lactose by Selective p-Toluenesulfonylation
• COLUMBIN ISOLATED FROM CALUMBAE RADIX AFFECTS THE SLEEPING TIME OF ANESTHETIZED MICE
• ISOLATION OF BILOBALIDE AND GINKGOLIDE A FROM GINKGO BILOBA L. SHORTEN THE SLEEPING TIME INDUCED IN MICE BY ANESTHETICS
• Studies on the Constituents of Edible and Medicinal Plants. III. Effects of Seven Limonoids on the Sleeping Time Induced in Mice by Anesthetics
• 2-Methyl-3-o-hydroxymethylphenyl-4 (3H)-quinazolinone, a Metabolite of 2-Methyl-3-o-tolyl-4 (3H)-quinazolinone in Rabbit
• Thiosugars. V. Synthesis of 1-Thio-β-D-ribopyranose and 1-Thio-β-D-mannopyranose Derivatives
• Thiosugars. VII. Synthesis of 1-Thio-2-deoxy-β-D-glucose Derivatives
• A New Synthesis of α-L-Fucose
• Chemical Modification of Lactose. X. Syntheses of 4-O-(3-O-Methyl-β-D-idopyranosyl)-D-glucopyranose and 4-O-(3-Deoxy-β-D-lyxo-hexopyranosyl)-D-glucopyranose
• Chemical Modification of Lactose. VII. Synthesis of 4-O-β-D-Idopyranosyl-D-glucopyranose
• Chemical Modification of Lactose. VII. Synthesis of 4-0-β-D-Idopyranosyl-D-glucopyranose
• Syntheses of 6-Acetamido-6-deoxy-lactose Derivatives
• Glucose Repression in Yeast Cells. Comparison of the Effect of Galactose with that of Glucose on the Formation of Respiratory Enzymes and Cytochromes
• Studies on the Metabolic Effects of Borate. VI. Effects of Borate on the Reduction of Methemoglobin
• Studies on the Metabolism of Borate. IV. Effect of Borate on Glyceraldehydephosphate Dehydrogenase.
• ホウ酸塩の代謝について(V) : 赤血球内の嫌気的解糖系ならびにメトヘモグロビン生成におよぼすホウ酸塩の影響について
• Studies on the Metabolism of Borate. III. Variations of Fructose 6-Phosphate Levels and Fructose 1,6-Diphosphate Levels in some Organs and Blood after Administration of Borate, and Effects of Boron on Anaerobic Glycolysis.
• Studies on Mercapturic Acids. Effect of Some Chemical Compounds on the Activities of Glutathione-conjugating Enzymes
• Thiosugars. VIII. Synthesis of 1,2-Dithio-β-D-mannopyranose
• Synthesis of 1,2-Di-S-acetyl-1,2-dithio-3,4,6-tri-O-acetyl-β-D-mannopyranose
• Studies on the Bromine Addition Compounds derived from 3,4,6-Tri-O-acetyl-D-glucal
• Thiousugars.X.Studies on Glycosyl N, N-Dialkyldithiocarbamates
• Studies on Nitro-Reducing Systems of Rat Liver
• キノン系化合物の抗菌性作用機序に関する研究(第2報) : キノン系化合物の抗菌性に対する諸種化合物の影響(その1)キノン系化合物の抗菌性に対する表面活性剤の影響
• Thiosugars.IX. Further Studies on the Anomalous Substitution of the Secondary Mesyl in Thiosugars
• Promoter function of carrageenan on development of colonic tumors induced by 1,2-dimethylhydrazine in rats.

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