Chemical Modification of Lactose. III. Syntheses of 4'-Acetamido-4'-deoxy-α-lactose and 6'-Acetamido-6'-deoxy-α-cellobiose

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概要

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• Syntheses of 4'-acetamido-4'-deoxy-α-lactose (12) and 6'-acetamido-6'-deoxy-α-cellobiose (19) are described starting from 1,6-anhydro-β-cellobiose (1) with seven steps. The sequence of the reaction is as follows. Selective tritylation and successive acetylation of 1 afford 1,6-anhydro-2,3,2', 3', 4'-penta-O-acetyl-6'-O-trityl-β-cellobiose (2), mp 191-192°, [α]^<23>_D -11°, in 45% yield. Detritylation of 2 with hydrogen bromide in acetic acid gives two products, crystalline 1,6-anhydro-2,3,2', 3', 6'-penta-O-acetyl-cellobiose (3) and sirupy 1,6-anhydro-2,3,2', 3', 4'-penta-O-acetyl-β-cellobiose (4), in a yield of approximately the equal amount. Sulfonylation of 3,substitution of the sulfonate with sodium azide, reduction of the azido-group, acetolysis of the 1,6-anhydro ring, and deacetylation afford 12. In the same manner, 19 is obtained from 4.

• 社団法人日本薬学会の論文
• 1973-11-25

著者

• 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

• 羽賀 正信

  Faculty Of Pharmaceutical Sciences Health Sciences University Of Hokkaido

• 岡森 克充

  Faculty of Pharmaceutical Sciences, Nagoya City University

• 岡森 克充

  Faculty Of Pharmaceutical Sciences Nagoya City University

関連論文

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