Chemical Modification of Maltose. V. A New Synthesis of 2-Acetamido-2-deoxy-4-O-α-D-glucopyranosyl-α-D-glucopyranose (N-Acetylmaltosamine)

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概要

• 論文の詳細を見る

• Crystalline 2', 3,3', 4', 6'-penta-O-acetyl-1,6-anhydro-β-N-acetylmaltosamine (10) was prepared in 7 steps from 1,6 : 2,3-di-anhydro-4-O-(4,6-O-benzylidene-2-O-tosyl-α-D-glucopyranosyl)-β-D-mannopyranose (3) as follows : benzylation, azidolysis of the oxirane ring, detosylation, debenzylidenation, acetylation, reduction of the azido to an amino group with concomitant debenzylation, and acetylation. Acetolysis of the 1,6-anhydro-β-ring of 3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-4-O-(2,4,6-tri-O-acetyl-3-O-benzyl-α-D-glucopyranosyl)-β-D-glucopyranose, which is the fifth intermediate in the synthesis of 10 from 3,yielded an anomeric mixture of the corresponding hexaacetates (12). Catalytic reduction of 12 followed by acetylation gave an anomeric mixture of 1,2', 3,3', 4', 6,6'-hepta-O-acetyl-N-acetylmaltosamines (13). De-O-acetylation of 13 gave the title disaccharide 17. The mp and [α] D values of 17 were in fairly good agreement with those of N-acetylmaltosamine synthesized by Sinay et al. [M.A.M. Nassr, J.-C. Jacquinet, and P. Sinay, Carbohydr. Res., 77,99 (1979)].

• 社団法人日本薬学会の論文
• 1981-07-25

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

  名古屋市立大学薬学部

• 手島 節三

  Faculty of Pharmaceutical Sciences, Nagoya City University

• 手島 節三

  Faculty Of Pharmaceutical Sciences Nagoya City University

• 森 雅美

  Faculty of Pharmaceutical Sciences, Nagoya City University

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