Thiosugars. VIII. Synthesis of 1,2-Dithio-β-D-mannopyranose

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概要

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• 1,2-Di-S-acetyl-1,2,-dithio-3,4,6-tri-O-acetyl-β-D-mannopyranose (IX) was obtained when a mixture of potassium thiolacetate and one of the 2-bromo-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl ethylxanthate (III), 2-bromo-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranosyl bromide (IV), 2-O-mesyl-3,4,6-tri-O-acetyl-β-D-glucopyranosyl ethylxanthate (VII) or 1-S-acetyl-1-thio-2-O-mesyl-3,4,6-tri-O-acetyl-β-D-glucopyranose (VIII) in acetone-ethanol was refluxed for five minutes. The title compound, hygroscopic sirup, [α]^22_D-109.3°→-34°(H_2O), was prepared by deacetylation of IX. Alkaline degradation of III or VII did not afford 1,2-dideoxy-1,2-epithio-β-D-mannopyranose, but gave amorphous powders (XVI), m.p. 108〜113°, [α]^28_D+77.8°(CHCl_3) after acetylation of the degradation product. Similarly, 4,6-O-benzylidene compound of III or VII (XVIII or XX) afforded amorphous powders (XXI), [α]^28_D+111°(CHCl_3). The structures of XVI and XXI were discussed and considered as polymeric products.

• 公益社団法人日本薬学会の論文
• 1966-06-25

著者

• 赤木 満洲雄

  Faculty of Pharmaceutical Sciences, School of Medicine, Hokkaido University

• 手島 節三

  Faculty of Pharmaceutical Sciences, Nagoya City University

• 手島 節三

  Faculty Of Pharmaceutical Sciences Nagoya City University

• 中村 博

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 赤木 満洲雄

  Faculty Of Pharmaceutical Sciences Hokkaido University

関連論文

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