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首页> 外文学位 >I. Sulfonium-mediated oxidative glycosylation of glycal donors for the synthesis of C(2)-hydroxy-beta-glycosides. II. Hypervalent iodine (III)-mediated oxidative glycosylation of glycal donors for the synthesis of C(2)-acyloxy-beta-glycosides. III. Efforts toward the synthesis of immunologic adjuvant QS-21A(api).
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I. Sulfonium-mediated oxidative glycosylation of glycal donors for the synthesis of C(2)-hydroxy-beta-glycosides. II. Hypervalent iodine (III)-mediated oxidative glycosylation of glycal donors for the synthesis of C(2)-acyloxy-beta-glycosides. III. Efforts toward the synthesis of immunologic adjuvant QS-21A(api).

机译：I.硫介导的葡萄糖供体的氧化糖基化反应，用于合成C（2）-羟基-β-糖苷。二。高价碘（III）介导的糖供体的氧化糖基化反应，用于合成C（2）-酰氧基-β-糖苷。三，致力于合成免疫佐剂QS-21A（api）。

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摘要

Development of two novel glycosylation procedures, and the synthesis of immunologic adjuvant QS-21Aapi is reported. In the first glycosylation procedure, glycals were employed as glycosyl donors and activated with a reagent combination of diphenyl sulfoxide and triflic anhydride. This sulfonium-mediated oxidative glycosylation procedure can be used for 1,2-trans-C2-hydroxy-β-glycoside synthesis with the application to assemble C2-branched oligosaccharides. In the second glycosylation procedure, glycals were activated with bisacyliodobenzene and boron trifluoride diethyl etherate for the synthesis of 1,2-trans -C2-acyloxy-β-glycoside with the application to assemble non-C2-branched oligosaccharides. In the third section of this thesis, an acylated triterpene glycoside QS-21Aapi was targeted for synthesis using the two oxidative glycosylation procedures as well as a sulfonium-mediated dehydrative glycosylation procedure. Synthesis and extraction of the four components of the saponin, which includes a trisaccharide, a tetrasaccharide, a triterpene and an acyl side chain were accomplished leading to the assembly of these four components to provide the fully protected QS-21Aapi.
机译：报道了两种新型糖基化方法的发展以及免疫佐剂QS-21A api 的合成。在第一个糖基化过程中，将糖用作糖基供体，并用二苯亚砜和三氟甲磺酸酐的试剂组合活化。该sulf介导的氧化糖基化方法可用于1,2- <斜体>反式 -C2-羟基-β-糖苷合成，并用于组装C2支链寡糖。在第二个糖基化程序中，用双酰基碘代苯和三氟化硼二乙基醚化物活化糖类，以合成1,2- <斜体>反式 -C2-酰氧基-β-糖苷，并用于组装非C2支链寡糖。在论文的第三部分中，使用两种氧化糖基化方法以及sulf介导的脱水糖基化方法，将酰化的三萜糖苷QS-21A api 靶向合成。皂素的四种成分的合成和提取包括三糖，四糖，三萜和酰基侧链，从而完成了这四种成分的组装，从而提供了受完全保护的QS-21A api 。

著录项

  • 作者

    Kim, Yong-Jae.;

  • 作者单位

    University of Illinois at Urbana-Champaign.;

  • 授予单位 University of Illinois at Urbana-Champaign.;
  • 学科 Chemistry Organic.; Chemistry Pharmaceutical.
  • 学位 Ph.D.
  • 年度 2003
  • 页码 263 p.
  • 总页数 263
  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 有机化学;药物化学;
  • 关键词

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