抄録
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.
