Chemical Modification of Maltose. IV. Synthesis of 4-O-α-D-Altropyranosyl-D-glucopyranose
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概要
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The new reducing disaccharide 4-O-α-D-altropyranosyl-D-glucopyranose (12) was synthesized by isomerization of secondary hydroxyl groups in the non-reducing part of maltose. Treatment of 1,6-anhydro-4', 6'-O-benzylidene-2,2'-di-O-tosyl-β-maltose (2) with methanolic sodium methoxide at room temperature gave the corresponding monoepoxide (3) in 90% yield, in which the oxirane ring is located in the reducing part of maltose. When the reaction was performed at boiling temperature, the diepoxide (5) having α-D-mannopyranosyl-D-mannopyranose configuration was obtained in 77% yield. Compound 5 was also obtainable from 2 in 79% yield. Heating a mixture of 5 and excess potassium hydroxide resulted in trans-diaxial cleavage of both oxirane rings, and 2,3-di-O-acetyl-1,6-anhydro-4-O-(2,3-di-O-acetyl-4,6-O-benzylidene-α-D-altropyranosyl)-β-D-glucopyranose (6) was isolated in 81.4% yield after acetylation of the cleavage product. Compound 6 was also obtainable from 2 in 59% yield. The disaccharide 12 was prepared as a hygroscopic amorphous powder after removal of the protecting groups of 6 as follows ; debenzylidenation, acetylation, acetolysis, and deacetylation.
- 社団法人日本薬学会の論文
- 1981-02-25
著者
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森 雅美
金城学院大学薬学部
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森 雅美
名古屋市立大学看護学部(生化学)
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森 雅美
愛知きわみ看護短期大学
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手島 節三
名古屋市立大学薬学部
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手島 節三
Faculty of Pharmaceutical Sciences, Nagoya City University
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手島 節三
Faculty Of Pharmaceutical Sciences Nagoya City University
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森 雅美
Faculty of Pharmaceutical Sciences, Nagoya City University
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