Chemical Modification of Lactose. X. Syntheses of 4-O-(3-O-Methyl-β-D-idopyranosyl)-D-glucopyranose and 4-O-(3-Deoxy-β-D-lyxo-hexopyranosyl)-D-glucopyranose

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概要

• 論文の詳細を見る

• The titled new reducing disaccharides were synthesized from a derivative of lactose. When 1,6-anhydro-4-O-(2,3-anhydro-4,6-O-benzylidene-β-D-glucopyranose (2) was treated with boiling methanolic sodium methoxide, or LiAlH_4 in boiling tetrahydrofuran, the trans-diaxial cleavage of the epoxide ring proceeded predominantly according to the Furst-Plattner rule. This agreed with the result obtained by treatment of 2 with KOH, reported previously [T. Chiba and S. Tejima, Chem. Pharm. Bull. (Tokyo), 25,1049 (1977)]. After acetylation, the major and minor cleavage products of epoxide were isolated by column chromatography on silica gel. The structural assignments of individual products were described. The titled disaccharides were respectively prepared from the individual major product via a series of the following reactions : debenzylidenation, acetylation, opening of the 1,6-anhydro ring, and removal of the acetyl groups.

• 公益社団法人日本薬学会の論文
• 1978-11-25

著者

• 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

• 千葉 拓

  Faculty of Pharmaceutical Sciences, Nagoya City University

• 手島 節三

  Faculty Of Pharmaceutical Sciences Nagoya City University

• 千葉 拓

  名古屋市立大学薬学部

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