Thiosugars. XII. Studies on Unsaturated Sugars derived from Glucosyl N, N-Dimethyldithiocarbamate.

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概要

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• 2-O-Mesyl-3,4,6-tri-O-acetyl-β-D-glucopyranosyl N, N-dialkyldithiocarbamate (VI or VII, VI : methyl, VII : ethyl) was prepared starting from the corresponding bromide by treatment with sodium N, N-dialkyldithiocarbamate (III or IV, III : methyl, IV : ethyl). Reflux of a mixture of VI or VII and potassium thiolacetate in acetone-ethanol afforded 2-S-acetyl-2-thio-3,4,6-tri-O-acetyl-β-D-mannopyranosyl N, N-dialkyldithiocarbamate (VIII or IX, VIII : methyl, IX : ethyl) in 30 to 40% yield. The structure was confirmed by UV, IR, NMR and the formation of 3,4,6-tri-O-acetyl-D-hydroglucal. When a mixture of VI and potassium acetate in acetone-ethanol was refluxed for one hour, crystals (XI), m.p. 104°, [α]^<20>_D+185.8° were obtained in 93% yield. The product was also obtainable by acetylation of 1,2-dideoxy-1,2-(N, N-dimethylammonium)-dithiocarbonyl-β-D-mannopyranose methanesulfonate (XIII) which was prerared starting from VI, by deacetylation and successive evaporation of an aqueous solution of the deacetylated product. The structure of XI was assigned to be 2-N, N-dimethyldithiocarbamoyl-2-deoxy-3,4,6-tri-O-acetyl-D-arabino-hexopyranose-1-ene, and the reaction mechanism of the formation was discussed. Deacetylation of XI afforded 2-N, N-dimethyldithiocarbamoyl-2-deoxy-D-arabino-hexopyranose-1-ene (XIV), m.p. 157°, [α]^<20>_D+131.9° which is a new type of unsaturated sugars. The nuclear magnetic resonance spectroscopy helped greatly in the determination of the structures of compounds in this series.

• 社団法人日本薬学会の論文
• 1967-10-25

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)
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• Thiosugars. VI. Reaction Products of Potassium Alkyl- and Benzylxanthates with Acetylated Glucosyl Halides.
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• Biochemical Studies on Thiosugars. I. Synthesis of 1-Thio-D-glucuronic Acid.
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• Studies on the Bromine Addition Compounds derived from 3,4,6-Tri-O-acetyl-D-glucal
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