Thiosugars. XV. Further Contribution on Anomalous High Reactivity of Secondary Methanesulfonic Esters in Thiosugars

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概要

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• 1,2-Di-S-acetyl-3,4,6-tri-O-acetyl-β-D-mannopyranose (X) and methyl 1,2-dithio-2-S-methyl-3,4,6-tri-O-acetyl-β-D-mannopyranoside (XI) were synthesized using an unequivocal route. A detailed comparison of the physical constants and NMR data of X with those of 1,2-di-S-acetyl-3,4,6-tri-O-acetyl-β-D-mannopyranose, which had been reported from our laboratory (H. Nakamura, S. Tejima, M. Akagi, Chem. Pharm. Bull. (Tokyo), 14,648 (1966).) clarified that the previous compound (VI) was the α-anomer of X. The corresponding methyl 1,2-dithio-2-S-methyl-3,4,6-tri-O-acetyl-α-D-mannopyranoside (VII) was prepared from VI. Reaction of potassium thiolacetate with 2-O-mesyl-3,4,6-tri-O-acetyl-β-D-glucopyranosyl N, N-dimethyldithiocarbamate (XVI) afforded three products (XVII, XVIII, VIII) in proportions of 5 : 2 : 3. The structure of the main product (XVII), which had been assigned as 1,2-dithio-1-N, N-dimethyldithiocarbamoyl-2-S-acetyl-3,4,6-tri-O-acetyl-β-D-mannopyranose (S. Ishiguro, S. Tejima, Chem. Pharm. Bull. (Tokyo), 15,1478 (1967).), was corrected to 1,2-dithio-1-S-acetyl-2-N, N-dimethyldithiocarbamoyl-3,4,6-tri-O-acetyl-β-D-mannopyranose. The by-products, XVIII and VIII, were assigned as 2-N, N-dimethyldithiocarbamoyl-2-deoxy-3,4,6-tri-O-acetyl-D-arabino-hexopyranose-1-ene and 1,2-dideoxy-1,2-trithiocarbonyl-3,4,6-tri-O-acetyl-β-D-mannopyranose, respectively. The reaction mechanisms on the facile substitution of secondary mesyl in thiosugars, which may be more reasonable than before, were discussed.

• 社団法人日本薬学会の論文
• 1969-12-25

著者

• 阪田 正勝

  東日本学園大学薬学部

• 阪田 正勝

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 手島 節三

  Faculty of Pharmaceutical Sciences, Nagoya City University

• 羽賀 正信

  東日本学園大学薬学部

• 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

  公立昭和病院

• Haga M

  Faculty Of Pharmaceutical Sciences Health Sciences University Of Hokkaido

• Haga Masanobu

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 羽賀 正信

  Faculty Of Pharmaceutical Sciences Health Sciences University Of Hokkaido

• 石黒 駿

  Kyorin Chemical Laboratory

• 石黒 駿

  Faculty of Pharmaceutical Sciences, Hokkaido University

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