Thiosugars. XIII. An Attempt at Thiosugar Synthesis having a Vicinal cis-Dimercapto Group in the Pyranose Ring

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概要

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• Methyl 2,3-dideoxy-2,3-dimercapto-α-D-mannopyranoside, isolated as sirupy tetraacetate (XIII), was synthesized in 13% yield by reduction of methyl 2,3-dithio-4,6-O-benzylidene-α-D-mannopyranoside 2,3-S-carbonate (IX) with sodium in liquid ammonia. The product was also obtainable in the same yield by alkaline treatment of methyl 2,3-dithio-4,6-di-O-acetyl-α-D-mannopyranoside 2,3-S-carbonate (XII). Dithiocarbonate (IX), a key intermediate of the synthesis was obtained by the following route : epoxide opening in methyl 2,3-anhydro-4,6-O-benzylidene-α-D-allopyranoside (II) with sodium N, N-dimethyldithiocarbamate (I) to give methyl 2-deoxy-2 (N, N-dimethyl dithiocarbamoyl)-4,6-O-benzylidene-α-D-altropyranoside (III), sulfonation of III, and successive intramolecular ring formation in the pyranose ring involving trans-diaxial elimination by treatment of the sulfonate (VII or VIII) with potassium acetate.

• 社団法人日本薬学会の論文
• 1968-08-25

著者

• 手島 節三

  Faculty of Pharmaceutical Sciences, Nagoya City University

• 手島 節三

  Faculty Of Pharmaceutical Sciences Nagoya City University

• 石黒 駿

  Kyorin Chemical Laboratory

• 石黒 駿

  Faculty of Pharmaceutical Sciences, Hokkaido University

関連論文

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• 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
• 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
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• 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
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• 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
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• Studies on the Fischer's Glucal-hydrobromid-diacetat and Glucal-hydrobromid-triacetat
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• 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.
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• 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
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• 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
• 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
• 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
• 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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