Syntheses of Two Pairs of Enantiomeric C18-Sphingosines and a Palmitoyl Analogue of Gaucher Spleen Glucocerebroside

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概要

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• Sixteen kinds of chiral C4-epoxides [(-)-10a-d, (+)-10a-d, (-)-11a-d, (+)-11a-d], which are synthons in our synthetic strategy for complex lipids, have been prepared from (2Z)-2-butene-1,4-diol (6) by employing a Sharpless asymmetric epoxidation. By using the chiral C4-epoxides [(+)-10a, (-)-10a, (-)-11a, (+)-11a] as starting compounds, two pairs of enantiomeric (D-erythro, L-erythro, D-threo, and L-threo)-C18-sphingosines (1,2,3,4) have been synthesized via a regioselective ring-opening of the epoxide ring with azide anion followed by reduction of the azide group to an amino group and a Wittig reaction. Furthermore, D-erythro-C18-sphingosine (1) has been converted to a palmitoyl analogue (5a) of Gaucher spleen glucocerebroside (5) through a reaction pathway including successive condensations with palmitic acid and D-glucose.

• 社団法人日本薬学会の論文
• 1992-05-25

著者

• 北川 勲

  Faculty of Pharmaceutical Sciences, Osaka University

• 成田 憲彦

  大阪大学薬学部

• 渋谷 博孝

  Faculty of Pharmaceutical Sciences, Osaka University

• 成田 憲彦

  Faculty of Pharmaceutical Sciences, Osaka University

• 川嶋 恵子

  大阪大学薬学部

• 池田 雅彦

  大阪大学薬学部

• 川嶋 恵子

  Faculty of Pharmaceutical Sciences, Osaka University

• 池田 雅彦

  Faculty of Pharmaceutical Sciences, Osaka University

• 北川 勲

  Faculty Of Pharmaceutical Sciences Osaka University

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