Thiosugars. XVII. Syntheses of Maltose Derivatives having Sulfur Atom in the Reducing Moiety

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概要

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• Several maltose derivatives containing sulfur atom in C_1 and C_6 positions in maltose have been synthesized. Treatment of maltosan hexaacetate (II) with titanium tetrabromide in chloroform, followed by acetylation with mercuric acetate in acetic acid, afforded 1,2,3,2', 3', 4', 6'-hepta-O-acetyl-β-maltose (III) in 41% yield. Heating of the corresponding 6-tosylate (V) with potassium thiolacetate in N, N-dimethylformamide afforded 1,2,3,2', 3', 4', 6'-hepta-O-acetyl-6-S-acetyl-6-deoxy-6-thio-β-maltose (VII). Deacetylation of VII gave 6-deoxy-6-thio-maltose (IX) as a sirup which contained two products, disulfide and thiol. Starting from 6-mesylate (IV) or 6-tosylate (V), crystalline 1,6-anhydro-2,3,2', 3', 4', 6'-hexa-O-acetyl-6-deoxy-6-thio-β-maltose (6-thiomaltosan hexaacetate) (XV) was synthesized by an analogous reaction sequence describing in the preparation of 6-thiolactosan hexaacetate ; S. Tejima, Carbohyd. Res., 20,123 (1971). Deacetylation of XV afforded 1,6-anhydro-6-deoxy-6-thio-β-maltose (6-thiomaltosan) (XIX) as amorphous powders. Acetolysisof XV gave 1,2,3,2', 3', 4', 6'-hepta-O-acetyl-6-deoxy-6-thio-6-S-acetyl-α-maltose (XVIII). Reductive desulfurization of XV, followed by deacetylation, yielded 1,5-anhydro-4-O-α-D-glucopyranosyl-6-deoxy-D-glucitol (XVII) as amorphous powders. Syntheses of several 1-thio-β-maltose derivatives have also been described.

• 社団法人日本薬学会の論文
• 1974-06-25

著者

• 森 雅美

  金城学院大学薬学部

• 森 雅美

  名古屋市立大学看護学部(生化学)

• 森 雅美

  愛知きわみ看護短期大学

• 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

• 森 雅美

  Faculty of Pharmaceutical Sciences, Nagoya City University

• 羽賀 正信

  Faculty Of Pharmaceutical Sciences Health Sciences University Of Hokkaido

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