Studies on the Fischer's Glucal-hydrobromid-diacetat and Glucal-hydrobromid-triacetat
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概要
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Reaction of hydrogen bromide in glacial acetic acid upon 3,4,6-tri-O-acetyl-D-glucal and successive treatment of the reaction product with aqueous acetone under the presence of silver carbonate afforded crystals (V), mp 99°, [α]^<20>_D+40.5°→+34.5°, in 70% yield. The product was also obtainable from 2,3-dideoxy-1,4,6-tri-O-acetyl-D-erythro-hex-2-enose or 2-deoxy-1,3,4,6-tetra-O-acetyl-α-D-arabino-hexopyranose in 70 or 50% yield. The structure of V was assigned to 3-bromo-4,6-di-O-acetyl-2,3-dideoxy-α-arabino-hexo-pyranose. Acetylation of V with acetic anhydride in pyridine gave crystals (VI), mp 82°, [α]^<20>_D+58°, in 85% yield. The structure of VI was assigned to 3-bromo-2,3-dideoxy-1,4,6-tri-O-acetyl-α-D-arabino-hexopyranose. The physical constants of V and VI were in agreement with that of the Fischer's Glucal-hydrobromid-diacetat and triacetat (E. Fischer, M. Berg-mann, and H. Schotte, Ber., 53,509 (1920)), which might presumably be the same compounds.
- 社団法人日本薬学会の論文
- 1968-11-25
著者
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手島 節三
Faculty of Pharmaceutical Sciences, Nagoya City University
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手島 節三
Faculty Of Pharmaceutical Sciences Nagoya City University
関連論文
- 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
- 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
- Thiosugars. XVIII. : Synthesis of 2-Acylamino-1,6-anhydro-2,6-dideoxy-6-thio-β-D-glucopyranose
- 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
- 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
- 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.