Syntheses of 4-O-α-D-Galactopyranosyl-D-glucopyranose and 4-O-(6-Deoxy-α-D-galactopyranosyl)-D-glucopyranose by Chemical Modifications of Maltose

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概要

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• The title compounds were synthesized starting from 1,6-anhydro-β-maltose, via 1,6-anhydro-4', 6'-O-benzylidene-β-maltose with several steps. Heating of 2,2', 3,3'-tetra-O-acetyl-1,6-anhydro-4', 6'-di-O-mesyl-β-maltose (9) with sodium benzoate in hexamethylphosphosphoric triamide afforded 2,3-di-O-acetyl-1,6-anhydro-4-O-(2,3-di-O-acetyl-4,6-di-O-benzoyl-α-D-galactopyranosyl)-β-D-glucopyranose (15) as an amorphous powder. Deacylation of 15 and sequential reacetylation gave crystalline hexaacetate (16). The former of the title compound (19), mp 227-229,[α]^<26>_D+159.6°, was obtained after acetolysis of 16 followed by deacetylation. Treatment of 9 with NaI in acetonitrile effected substitution of the mesyloxy at C_<6'> to give the corresponding 6'-deoxy-6'-iodo-4'-O-mesyl derivative (11), from which 6'-deoxy compound (13) was prepared by catalytic hydrogenation. Benzoyloxy substitution with inversion at C_<4'>-mesyloxy in 13 gave 2,3-di-O-acetyl-1,6-anhydro-4-O-(2,3-di-O-acetyl-4-O-benzoyl-6-deoxy-α-D-galactopyranosyl)-β-D-glucopyranose (20), from which the latter of the title compound (24), hydroscopic, amorphous powder, [α]^<27>_D+128.3°, was obtained via the same pathway as for 19 from 15. Synthesis and characterization of the key intermediate (9) were described in full detail.

• 社団法人日本薬学会の論文
• 1975-07-25

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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