Studies on the Bromine Addition Compounds derived from 3,4,6-Tri-O-acetyl-D-glucal

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概要

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• The works on the bromination of 3,4,6-tri-O-acetyl-D-glucal and methanolysis of the product which had been reported by Fischer, Bergmann, and Schotte (Ber., 53,509 (1920)) were restudied. The strctures of the two crystalline compounds termed the "triacetyl-methylglucoside-2-bromohydrins I and II" were demonstrated as methyl 2-bromo-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranoside and methyl 2-bromo-2-deoxy-3,4,6-tri-O-acetyl-β-D-mannopyranoside, respectively. 2-Bromo-2-deoxy-1,3,4,6-tetra-O-acetyl-β-D-glucopyranose (X) was prepared as a crystalline form. Crystalline, stable bromide (XI) was prepared starting from X, and assigned as 2-bromo-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranosyl bromide which was not identical with the labile bromide by Fischer, et al. The nuclear magnetic resonance spectra presented a further proof for the configurations at C1 and C2 in X and XI.

• 公益社団法人日本薬学会の論文
• 1964-11-25

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

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