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首页> 外文期刊>Chemistry: A European journal >From D-Glucose to Biologically Potent L-Hexose Derivatives:Synthesis of alpha-L-Iduronidase Fluorgenic Dector and the Disaccharide Moieties of Bleomycin A_2 and Heparan Sulfate
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From D-Glucose to Biologically Potent L-Hexose Derivatives:Synthesis of alpha-L-Iduronidase Fluorgenic Dector and the Disaccharide Moieties of Bleomycin A_2 and Heparan Sulfate

机译：从D-葡萄糖到具有生物活性的L-己糖衍生物：α-L-异泛酸酶荧光分子的合成及博来霉素A_2和硫酸乙酰肝素的二糖部分

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摘要

A novel and convenient route for the synthesis of biologically potent and rare L-hexose derivatives from D-glucose is described.Conversion of diacetone-alpha-D-glucose (14) into 1,2:3,5-di-O-isopropylidene-beta-L-idofuranose (19) was efficiently carried out in two steps.Orthogonal isopropylidene rearrangement of compound 19 led to 1,2:5,6-di-O-isopropylidene-beta-L-idofuranose (27),which underwent regioselective epimerization at the C3 position to give the L-talo- and 3-functionalized L-idofuranosyl derivatives.Hydrolysis of compound 19 under acidic conditions furnished 1,6-anhydro-beta-L-idopyranose (35) in excellent yield,which was successfully transformed into the corresponding L-allo,L-altro,L-gulo,and L-ido derivatives via regioselective benzylation,benzoylation,triflation and nucleophilic substitution as the key steps.Applications of these 1,6-anhydro-beta-L-hexopyranoses as valuable building blocks to the syntheses of 4-methylcoumarin-7-yl-alpha-iduronic acid and the disaccharide moieties of bleomycin A_2 as well as heparan sulfate are highlighted.
机译：描述了一种从D-葡萄糖合成生物有效且稀有的L-己糖衍生物的新颖便捷途径。双丙酮α-D-葡萄糖（14）转化为1,2：3,5-二-O-异亚丙基β-L-异呋喃糖（19）分两步有效进行。化合物19的正交异亚丙基重排导致1,2：5,6-二-O-异亚丙基-β-L-异呋喃糖（27）在C3位置进行区域选择性差向异构，得到L-talo-和3-官能化的L-idofuranosyl衍生物。在酸性条件下化合物19的水解提供了1,6-脱水β-L-idopyranose（35）的优异产率，通过区域选择性苄基化，苯甲酰化，三氟甲基化和亲核取代成功地转化为相应的L-allo，L-altro，L-gulo和L-ido衍生物。这些1,6-脱水β-L-的应用六吡喃糖是4-甲基香豆素-7-基-α-艾杜糖醛酸和二糖的合成的重要组成部分突出显示了博来霉素A_2和硫酸乙酰肝素的部分。

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