Name: synthesis and purification of iodoaziridines involving quantitative selection of the optimal stationary phase for chromatography
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Description: Watch this Scientific Journal Video about Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography at JoVE.com

对于财政的支持，我们非常感谢EPSRC（职业加速奖学金到申诉; EP/J001538/1），拉姆齐纪念信托（研究奖学金2009-2011 JAB），和伦敦帝国学院。谢谢教授艾伦·阿姆斯特朗的慷慨支持和建议。

Iodoaziridines 1。准备与Diiodomethyllithium <ol><li>火焰干燥含有搅拌棒并配备有隔膜，在氩气气流下在100毫升圆底烧瓶中，然后允许在氩气氛下冷却至室温。注：玻璃在烘箱中干燥过夜（125℃），并冷却至室温以类似的方式也是合适的。 </li><li>到烧瓶中， 通过微量添加5.7毫升无水THF和2.7毫升无水Et 2 O等，通过注射器，和新蒸馏的六甲基二硅烷（1.50毫摩尔，315微升）。 </li><li>搅?...

<ol>
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一个程序的顺式非对映选择性制备- N-TS-iodoaziridines进行了说明，连同稳定性研究协议来定量表示通过快速柱色谱法的最佳固定相的潜在不稳定的化合物的纯化。可以设想，通过这种方法获得iodoaziridines将使方法来访问了广泛的氮丙啶被开发，通过完整环的衍生化。 适当修改的程序亚胺与α-质子，是用亚胺 - 甲苯亚磺酸的加合物作为原料代替亚胺的材料由于改进的...

该方法的目的是制备iodoaziridines，提供潜力进一步官能化，以氮丙啶衍生物。该方法包含一个协议，用于定量选择最佳固定相的色谱。 氮丙啶，为三元环，posses固有的环张力，使有机化学其中1重要组成部分。他们的反应显示了浩大常累及氮丙啶开环2,3，特别是在官能胺4,5的合成中间体，或其他含氮杂环化合物6,7的形成。一系列由包含一个完整的氮丙啶环的前体官能氮丙啶衍生物的合成已成为一个可行的策略8。官能团 - 金属交换，以产生一个氮丙啶基的阴离子，并与亲电子反应已经被证明是有效<su对&gt; 9,10,11，和最近区域选择性和立体选择性的N-保护的氮丙啶的去质子化方面也取得了12-15。最近，钯催化的交叉偶联方法，形成由官能氮丙啶的前体芳基氮丙啶已开发Vedejs 16,17，和自己18。 的杂原子取代的吖丙啶化学开辟了反应性和稳定性19的有趣的问题。我们一直关心iodoaziridines的编制作为提供可能提供的前体范围广衍生物具有互补的反应，以现有的氮丙啶官能化反应的一种新的官能团。在2012年我们报道的芳基的N-Boc-iodoaziridines 20的第一个准备，最近报道的芳基和烷基取代的N-TS-iodoaziridines 21的准备。 该方法对ACCESS iodoaziridines使用diiodomethyllithium，最近也被用在diiodoalkanes 22,23的制备试剂，diiodomethylsilanes 22,24和乙烯基碘化物25-27。该试剂的卡宾样性质要 ​​求编制和使用在低温下22,28。在iodoaziridines编制用于diiodomethyllithium的产生的技术和条件说明如下。 而二氧化硅已成为首选色谱29的材料，它被证明是不适宜的N-TS-iodoaziridines的纯化。硅胶通常是在有机化学快速色谱由于可用性和有效的分离采用的第一个也是唯一的固相物质。然而，硅胶的酸性性质可以在纯化过程中会引起敏感的底物的分解，防止了所需材料的隔离。而其他STationary阶段或改性硅胶可用于色谱30，没有办法来评估这些不同材料的靶标分子的相容性。由于iodoaziridines的敏感性质，我们建立了一个协议，以评估化合物的稳定性固定相21，这是这里展示的数组。这具有在很宽范围内具有灵敏的官能团的化合物的合成中的应用潜力。下面的协议提供了有效的访问的N-TS iodoaziridines，允许两个烷基和芳顺 iodoaziridines高产率的非对映选择性合成。

<table border="0" cellpadding="0" cellspacing="0" width="871">
	<tbody>
		<tr height="42">
			<td height="42" style="height:42px;width:209px;">Hexamethyldisilazane</td>
			<td style="width:273px;">999-97-3</td>
			<td style="width:197px;">Alfa Aesar</td>
			<td style="width:192px;">Distill from KOH under argon prior to use.</td>
		</tr>
		<tr height="42">
			<td height="42" style="height:42px;width:209px;">n-Butyllithium</td>
			<td style="width:273px;">109-72-8</td>
			<td style="width:197px;">Sigma Aldrich</td>
			<td style="width:192px;">2.5 M in hexanes, titrate prior to use.</td>
		</tr>
		<tr height="42">
			<td height="42" style="height:42px;width:209px;">Diiodomethane</td>
			<td style="width:273px;">75-11-6</td>
			<td style="width:197px;">Alfa Aesar</td>
			<td style="width:192px;">Contains copper as a stabilizer.</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:209px;">1,3,5-Trimethoxybenzene</td>
			<td style="width:273px;">621-23-8</td>
			<td style="width:197px;">Sigma Aldrich</td>
			<td style="width:192px;"></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:209px;">Silica</td>
			<td style="width:273px;">112945-52-5</td>
			<td style="width:197px;">Merck</td>
			<td style="width:192px;"></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:209px;">Basic alumina</td>
			<td style="width:273px;">1344-28-1</td>
			<td style="width:197px;">Sigma Aldrich</td>
			<td style="width:192px;"></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:209px;">Neutral alumina</td>
			<td style="width:273px;">1344-28-1</td>
			<td style="width:197px;">Merck</td>
			<td style="width:192px;"></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:209px;">Florisil</td>
			<td style="width:273px;">1343-88-0</td>
			<td style="width:197px;">Sigma Aldrich</td>
			<td style="width:192px;"></td>
		</tr>
		<tr height="22">
			<td height="22" style="height:23px;width:209px;">THF</td>
			<td colspan="3" rowspan="3" style="width:663px;">All anhydrous solvents were dried through activated alumina purification columns.&#160;</td>
		</tr>
		<tr height="25">
			<td height="25" style="height:25px;width:209px;">Et2O</td>
		</tr>
		<tr height="25">
			<td height="25" style="height:25px;width:209px;">CH2Cl2</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;">NMR spectrometer</td>
			<td>Bruker AV 400&#160;</td>
			<td>n/a</td>
			<td></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:209px;">NMR processing software</td>
			<td>MestReNova&#160;</td>
			<td>7.0.2-8636</td>
			<td></td>
		</tr>
	</tbody>
</table>

synthesis and purification of iodoaziridines involving quantitative selection of the optimal stationary phase for chromatography

高非对映选择性制备顺式 -通过diiodomethyllithium与N-TS醛亚胺反应的N-TS-iodoaziridines描述。 Diiodomethyllithium通过二碘甲烷与将LiHMDS的去质子化制得，于THF /乙醚混合物中，在-78℃下 在黑暗中。这些条件是所产生的荔枝2试剂的稳定至关重要。随后滴加N-TS醛亚胺对预制diiodomethyllithium溶液，得到一种氨基-二碘化中间体，这是不隔离。将反应混合物至0℃的迅速升温促进环化反应，得到iodoaziridines用专用的顺式非对映选择性。该反应的加成和环化阶段被小心控制温度介导在一个反应​​烧瓶中。 由于iodoaziridines来净化，PU合适的方法评估的敏感性rification是必需的。一个协议，以评估敏感的化合物的稳定性，为柱层析固定相进行描述。这种方法适合于应用到新iodoaziridines，或其他潜在的敏感的新化合物。因此该方法可以应用于合成的项目范围。该过程涉及首先反应产率，在纯化前，通过1 H NMR谱与对比内部标准进行评估。不纯的产物混合物的部分则暴露于适合各种色谱固定相的淤浆，在适合于作为在闪式色谱洗脱剂的溶剂体系。搅拌30分钟，以模仿色谱法，随后进行过滤后，将样品的1 H核磁共振光谱仪进行分析。对于每个固定的相位计算出的产量进行比较，以从粗反应混合物最初获得的。所得结果可为T的定量评估该化合物的不同固定相的他的稳定性;因此，最佳的可选择。碱性氧化铝的选择，修改为活动四，作为一个合适的固定相已经允许某些iodoaziridines隔离的优良率和纯度。

该过程描述能提供顺式 - （±）-2 -碘-3 - （4 -甲苯基）-1 - （4 -甲苯磺酰基）氮丙啶作为单一对映异构体和具有优异的纯度（ 图1）。在纯化前，对iodoaziridine产品的59％的产率进行了计算，用1 H NMR谱。然而，这iodoaziridine是特别具有挑战性的净化和经历显著分解的二氧化硅。如通过固定相来确定屏幕上的纯化碱性氧化铝（活性Ⅳ）所允许的产品来进行分离产率为48...

Watch this Scientific Journal Video about Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography at JoVE.com

Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography

合成和Iodoaziridines纯化涉及定量选择最优固定相的色谱

一个协议的非对映选择性一锅准备顺 - N-TS-iodoaziridines描述。的diiodomethyllithium，除了N-TS醛亚胺和氨基宝石 -二碘化中间体iodoaziridines被证实环化生成。还包括的是一种协议通过色谱法快速和定量评估的最合适的固定相进行纯化。

The highly diastereoselective preparation of cis-N-Ts-iodoaziridines through reaction of diiodomethyllithium with N-Ts aldimines is described. ...

Research

JoVE Journal

Chemistry

Determination of the Gas-phase Acidities of Oligopeptides

寡肽测定气相酸性

Amino acid residues located at different positions in folded proteins often exhibit different degrees of acidities. For example, a cysteine residue ...

科研

化学

Split-and-pool Synthesis and Characterization of Peptide Tertiary Amide Library

分裂和池合成及肽叔酰胺图书馆表征

Peptidomimetics are great sources of protein ligands. The oligomeric nature of these compounds enables us to access large synthetic libraries on solid ...

Quantitative Detection of Trace Explosive Vapors by Programmed Temperature Desorption Gas Chromatography-Electron Capture Detector

定量检测痕量爆炸物蒸气通过程序升温脱附 - 气相色谱 - 电子捕获检测器

The direct liquid deposition of solution standards onto sorbent-filled thermal desorption tubes is used for the quantitative analysis of trace explosive ...

Supercritical Nitrogen Processing for the Purification of Reactive Porous Materials

超临界氮处理的活性多孔材料的净化

Supercritical fluid extraction and drying methods are well established in numerous applications for the synthesis and processing of porous materials. ...

A Quantitative Glycomics and Proteomics Combined Purification Strategy

定量糖组学和蛋白质组学组合式净化策略

There is a growing desire in the biological and clinical sciences to integrate and correlate multiple classes of biomolecules to unravel biology, define ...

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

协议的合成<em&gt;邻</em&gt; -trifluoromethoxylated苯胺类化合物

Molecules bearing trifluoromethoxy (OCF3) group often show desired pharmacological and biological properties. However, facile synthesis of ...

Synthesis of Protein Bioconjugates via Cysteine-maleimide Chemistry

Synthesis of Protein Bioconjugates via Cysteine-maleimide Chemistry

蛋白质生物缀合物的合成<em&gt;通过</em&gt;半胱氨酸马来酰亚胺化学

The chemical linking or bioconjugation of proteins to fluorescent dyes, drugs, polymers and other proteins has a broad range of applications, such as the ...

Protocol for the Solid-phase Synthesis of Oligomers of RNA Containing a 2'-O-thiophenylmethyl Modification and Characterization via Circular Dichroism

Protocol for the Solid-phase Synthesis of Oligomers of RNA Containing a 2'-O-thiophenylmethyl Modification and Characterization via Circular Dichroism

用于固相合成含有2&#39;-<em&gt; 0</em通过圆二色性修饰和表征

Solid-phase synthesis has been used to obtain canonical and modified polymers of nucleic acids, specifically of DNA or RNA, which has made it a popular ...

Synthesis and Mass Spectrometry Analysis of Oligo-peptoids

寡 peptoids 的合成及质谱分析

Peptoids are sequence-controlled peptide-mimicking oligomers consisting of N-alkylated glycine units. Among many potential applications, peptoids have ...