首页> 外文学位 >Synthetic studies of 3-deoxy-D-manno-2-octulosonic acid (KDO), 3-deoxy-D-arabino-2-heptulosonic acid (DAH), and their 4-epimers through the radical chemistry of Barton esters.

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Synthetic studies of 3-deoxy-D-manno-2-octulosonic acid (KDO), 3-deoxy-D-arabino-2-heptulosonic acid (DAH), and their 4-epimers through the radical chemistry of Barton esters.

机译：通过Barton酯的自由基化学合成3-deoxy-D-manno-2-octulosonic acid（KDO），3-deoxy-D-arabino-2-heptulosonic acid（DAH）及其4-epimers的合成研究。

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The radical chemistry of thiohydroxamates (Barton esters) was applied to the synthesis of the higher monosaccharides 3-deoxy-D-manno-2-octulosonic acid (KDO), 3-deoxy-D-arabino-2-heptulosonic acid (DAH), and their 4-epimers starting from commercial D-glucono-1,5-lactone and D-ribonolactone, respectively. DAH was synthesized in a concise manner and with good diastereoselectivity, for the first time, by radical chemistry.;The regeneration of the carbonyl group from phenylhydrazones by oxidation with hypervalent organoiodine reagents, benzeneseleninic anhydride (BSA), and nickel peroxide was studied. ;Acrylamide proved to be an effective radical trap for carbon radicals generated from Barton esters. By this radical chemistry, homologation of carboxylic acids to primary carboxamides and the synthesis of mesoionic compounds, namely the anhydro-2-alkyl-3-acyliminothiazolo (3,2-a) pyridinium hydroxide derivatives, were achieved.

机译：硫代羟肟酸酯（Barton酯）的自由基化学用于合成高级单糖3-deoxy-D-manno-2-octulosonic acid（KDO），3-deoxy-D-arabino-2-heptulosonic acid（DAH），它们的4-表位分别从商业D-葡萄糖基-1,5-内酯和D-核糖内酯开始。通过自由基化学方法，以简明的方式和良好的非对映选择性首次合成了DAH。研究了用高价有机碘试剂，苯硒二酸酐（BSA）和过氧化镍氧化从苯azo生成羰基的方法。；丙烯酰胺被证明是从Barton酯产生的碳自由基的有效自由基陷阱。通过这种自由基化学反应，将羧酸同化为伯羧酰胺，并合成了中性离子化合物，即脱水-2-烷基-3-酰基咪唑并（3,2-a）氢氧化吡啶鎓衍生物。

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作者
Liu, Wansheng.;
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Texas A&M University.;

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授予单位 Texas A&M University.;
学科 Organic chemistry.;Pharmacy sciences.
学位 Ph.D.
年度 1997
页码 222 p.
总页数 222
原文格式 PDF
正文语种 eng
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专利

1. THE INVENTION OF RADICAL REACTIONS .38. HOMOLOGATION OF CARBOXYLIC ACIDS WITH ACRYLAMIDE AND SYNTHETIC STUDIES OF 3-DEOXY-D-ARABINO-2-HEPTULOSONIC ACID (DAH) AND ITS 4-EPIMER [J] . Barton DHR., Liu WS. Tetrahedron . 1997,第36期

机译：自由基反应的发明.38。丙烯酰胺对羧酸的均质化以及3-脱氧-D-阿拉伯--2-庚酸（DAH）及其4-表异构体的合成研究
2. Alkylidenecarbene insertion at anomeric C-H bonds. Synthesis of 3-deoxy-D-arabino-2-heptulosonic acid (DAH) and 3-deoxy-D-manno-2-octulosonic acid (KDO) [J] . Duncan J.Wardrop, Wenming Zhang Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2002,第31期

机译：亚烷基卡宾在异头C-H键处插入。 3-脱氧-D-阿拉伯糖-2-庚基磺酸（DAH）和3-脱氧-D-甘露糖-2-辛基磺酸（KDO）的合成
3. THE INVENTION OF RADICAL REACTIONS .36. SYNTHETIC STUDIES RELATED TO 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID (KDO) [J] . Barton DHR., Liu WS., Shinada T., Tetrahedron . 1996,第8期

机译：自由基反应的发明.36。与3-DEOXY-D-MANNO-2-OCULSONSONIC ACID（KDO）相关的合成研究
4. Nitrilium Cations in the Spectra of N-Methyl-N-Perfluoroacyl-Amino Acids and Their Alkyl Esters. [C] . Nino G. Todua, Kirill V. Tretyakov, Anzor I. Mikaia ASMS Conference on Mass Spectrometry and Allied Topics . 2014

机译：在N-甲基-N-全氟乙基 - 氨基酸和它们的烷基酯的光谱中的氮阳离子。
5. Computational Quantum Chemistry Studies of the Interactions of Amino Acids Side Chains with the Guanine Radical Cation [D] . Acheampong, Edward. 2018

机译：氨基酸侧链与鸟嘌呤自由基阳离子相互作用的计算量子化学研究
6. The synthesis of the rhamnogalacturonan II component 3-deoxy-D-manno-2-octulosonic acid (Kdo) is required for pollen tube growth and elongation [O] . Frédéric Delmas, Martial Séveno, Julian G. B. Northey, -1

机译：鼠李糖半乳糖醛酸聚糖II组分3-deoxy-D-manno-2-octulosonic acid（Kdo）的合成是花粉管生长和伸长所必需的
7. Convenient Syntheses of 3-Deoxy-D-manno-2-octulosonic Acid (KDO) and 3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid (KDN) Derivatives from D-Mannose [O] . Ken-ichi Sato, Tomoyuki Miyata, Ikuo Tanai, 1994

机译：从D-甘露糖的3-脱氧-D-MANNO-2-辛膦酸（KDO）和3-脱氧-D-GLYCERO-D-GOLACTO-2-寡核酸（KDN）衍生物的方便合成。
8. Ab Initio Structures of Phosphorus Acids and Esters. 1. Phosphinic, Phosphonic and Phosphoric Acids. [R] . Ewig, C. S., van Wazer, J. R. 1985

机译：磷酸和酯的从头算结构。 1.次膦酸，膦酸和磷酸。

Synthetic studies of 3-deoxy-D-manno-2-octulosonic acid (KDO), 3-deoxy-D-arabino-2-heptulosonic acid (DAH), and their 4-epimers through the radical chemistry of Barton esters.

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