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首页> 外文学位 >I. Microwave-influenced diversity-oriented synthesis of biologically relevant small and natural-product-like molecules via multicomponent coupling reactions. II. Synthetic studies toward the total synthesis of the repeating tetrasaccharide unit of zwitterionic polysaccharide PS A1.
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I. Microwave-influenced diversity-oriented synthesis of biologically relevant small and natural-product-like molecules via multicomponent coupling reactions. II. Synthetic studies toward the total synthesis of the repeating tetrasaccharide unit of zwitterionic polysaccharide PS A1.

机译：I.通过多组分偶联反应，微波影响生物相关的小分子和天然产物样分子的面向多样性的合成。二。对两性离子多糖PS A1的重复四糖单元进行全合成的合成研究。

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摘要

Microwave-influenced diversity-oriented synthesis of biologically relevant small and natural-product-like molecules via multicomponent coupling reactions (MCCRs) have been investigated. Cheap, readily available starting materials in conjunction of microwave irradiation and employment of environmentally benign solvent (e.g. water) provided a common platform that allowed to access a wide array of structurally and skeletally diverse molecules. The investigation allowed us to establish a new paradigm of diversity-activity relationships (DARs) by tuning reacting components of the MCCRs and proved that in contrary to the conventional use of microwave as a rate accelerating tool, it can be used to influence reactivity of molecules. The method was also extended to develop new protecting groups (PGs, PDMAB, PMNPAB) that can be useful in carbohydrate as well as other areas of synthetic organic chemistry. Additionally, the new p-N,N-diemethylaminobenzyl (PDMAB) PG was employed to develop an alkoxide-based neutral glycosylation and further extended to study entirely neutral glycosylation via oxocarbenium ion.;We also investigated the total synthesis of the repeating tetrasaccharide unit of zwitterionic polysaccharide PS A1 using different strategies. PS A1 is known to modulate T-cell response via MHC-II pathway and shown to prevent tumor growth. The synthesis is quite challenging and we have been able to construct the trisaccharide unit of the repeating tetrasaccharide unit of PS A1.
机译：已经研究了通过微波影响的通过多组分偶联反应（MCCR）合成的生物学相关小分子和类天然产物的多样性导向合成。廉价，容易获得的原料，结合微波辐射和使用环境友好的溶剂（例如水），提供了一个通用平台，该平台可访问各种结构和骨架不同的分子。该研究使我们能够通过调节MCCR的反应成分建立新的多样性-活性关系（DARs）范式，并证明与常规使用微波作为速率加速工具相反，微波可用于影响分子的反应性。该方法还扩展为开发新的保护基（PG，PDMAB，PMNPAB），这些保护基可用于碳水化合物以及合成有机化学的其他领域。此外，新的pN，N-二甲基氨基苄基（PDMAB）PG被用于开发基于醇盐的中性糖基化，并进一步扩展以研究通过氧碳ion离子的完全中性糖基化。；我们还研究了两性离子多糖重复四糖单元的总合成PS A1使用不同的策略。已知PS A1可通过MHC-II途径调节T细胞反应，并显示可预防肿瘤生长。合成非常具有挑战性，我们已经能够构建PS A1重复四糖单元的三糖单元。

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  • 作者

    Santra, Soumava.;

  • 作者单位

    Wayne State University.;

  • 授予单位 Wayne State University.;
  • 学科 Chemistry Organic.
  • 学位 Ph.D.
  • 年度 2010
  • 页码 975 p.
  • 总页数 975
  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类
  • 关键词

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