Chemical Modification of Lactose. V. Synthesis of 6'-Acetamido-6'-deoxy-α-lactose

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概要

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• Benzylidenation of 1,6-anhydro-β-lactose afforded 1,6-anhydro-4', 6'-O-benzylidene-β-lactose (2) in 81% yield. Acylation of 2 yielded tetra-O-acyl-1,6-anhydro-4', 6'-O-benzylidene-β-lactose [acyl=acetyl (3), benzoyl (4)]. Reflux of 3 with N-bromosuccinimide and BaCO_3 in CCl_4 and 1,2-dichloroethane gave crystalline tetra-O-acetyl-1,6-anhydro-4'-O-benzoyl-6'-bromo-6'-deoxy-β-lactose (5) in 52% yield. Catalytic dehydrobromination of 5 afforded crystalline tetra-O-acetyl-1,6-anhydro-4'-O-benzoyl-6'-deoxy-β-lactose (6). Deacylation of 5 and successive reacetylation yielded 2,2', 3,3', 4'-penta-O-acetyl-1,6-anhydro-6'-bromo-6'-deoxy-β-lactose (7). Dehydrobromination of 7 gave penta-O-acetyl-1,6-anhydro-6'-deoxy-β-lactose (8). Heating of 7 and sodium azide in hexamethylphosphoric triamide afforded a mixture of crystalline penta-O-acetyl-1,6-anhydro-6'-azido-6'-deoxy-β-lactose (9) (36%) and sirupy 2,3-di-O-acetyl-1,6-anhydro-4-O-(2,3,4-tri-O-acetyl-α-L-arabino-hex-5-eno-pyranosyl)-β-D-glucopyranose (10) (34%). Compound 10 was also prepared by treatment of 7 in dry pyridine with silver fluoride. Acetolysis of 9,reduction of the azido group in the acetolysis product (11), N-acetylation, and finally de-O-acetylation afforded the title compound (13) as hydroscopic crystals, [α]^<24>_D+80°→+66.7°. In catalytic hydrogenation of 10 over Pd catalyst, 8 was the sole product in 90% yield. Over Pt oxide or Raney Ni catalyst, a low yield of 8 was effected with fairly amounts of unidentified sirup.

• 社団法人日本薬学会の論文
• 1975-06-25

著者

• 手島 節三

  Faculty of Pharmaceutical Sciences, Nagoya City University

• 千葉 拓

  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

• 千葉 拓

  名古屋市立大学薬学部

関連論文

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