A New Synthesis of α-L-Fucose

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概要

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• A new synthesis of α-L-fucose from D-glucose is described. The key intermediate is methyl 2,3-di-O-acetyl-4,6-O-benzylidene-α-D-altropyranoside (1), synthesized from methyl α-D-glucopyranoside by known procedures. Compound 1 was converted into methyl 2,3-di-O-acetyl-4-O-benzoyl-6-bromo-6-deoxy-α-D-altropyranoside (2) by treatment with N-bromosuccinimide. Dehydrobromination of 2 afforded the 5,6-unsaturated glycoside (4), which underwent reduction by hydrogen, mainly with inversion at C-5,to give methyl 2,3-di-O-acetyl-4-O-benzoyl-6-deoxy-β-L-galactopyranoside (5) with a small amount of the isomeric methyl 2,3-di-O-acetyl-4-O-benzoyl-6-deoxy-α-D-altropyranoside (3). The ratio of 3 to 5 was about 1 to 4. Deacylation of a mixture of 3 and 5 gave crystalline methyl β-L-fucopyranoside (6) and a syrupy methyl 6-deoxy-α-D-altropyranoside. Acidic hydrolysis of 6 afforded crystalline α-L-fucose in 19.3% yield from 1 via 5 steps.

• 公益社団法人日本薬学会の論文
• 1979-11-25

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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