t-butyl trans-5-(iodomethyl)-2-oxo-tetrahydrofuran-3-ylcarbamate | 150566-52-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: t-butyl trans-5-(iodomethyl)-2-oxo-tetrahydrofuran-3-ylcarbamate
• 英文别名: tert-butyl N-[(3R,5S)-5-(iodomethyl)-2-oxooxolan-3-yl]carbamate
• CAS: 150566-52-2
• 化学式: C₁₀H₁₆INO₄
• 分子量: 341.146
• InChiKey: MHDLRVDHFSLXGO-NKWVEPMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 t-butyl trans-5-(iodomethyl)-2-oxo-tetrahydrofuran-3-ylcarbamate 生成 N-BOC-反式-4-羟基-D-脯氨酸甲酯
  参考文献：
  名称：

  Asymmetric synthesis of α-amino acids through α-iodination of chiral unsaturated carboxamides and stereoselective iodolactonization

  摘要：

  The alpha-iodination reaction of chiral enamides 1 possessing (2R,5R)-2,5-bis(methoxymethyl)pyrrolidine as a chiral auxiliary proceeded with high diastereoselectivity in the presence of I2 and s-collidine. The chiral iodides 2 thus obtained were converted to the alpha-BocNH-amides 3 without epimerization. The subsequent iodolactonization afforded trans-lactones 4 with a relatively high selectivity.

  DOI：

  10.1016/s0040-4039(00)60372-6
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 碘 、 sodium carbonate 、 tin(ll) chloride 作用下， 以 乙醇 、 水 为溶剂， 反应 41.0h， 生成 t-butyl trans-5-(iodomethyl)-2-oxo-tetrahydrofuran-3-ylcarbamate
  参考文献：
  名称：

  Asymmetric synthesis of α-amino acids through α-iodination of chiral unsaturated carboxamides and stereoselective iodolactonization

  摘要：

  The alpha-iodination reaction of chiral enamides 1 possessing (2R,5R)-2,5-bis(methoxymethyl)pyrrolidine as a chiral auxiliary proceeded with high diastereoselectivity in the presence of I2 and s-collidine. The chiral iodides 2 thus obtained were converted to the alpha-BocNH-amides 3 without epimerization. The subsequent iodolactonization afforded trans-lactones 4 with a relatively high selectivity.

  DOI：

  10.1016/s0040-4039(00)60372-6

文献信息

• Modified N-acyl-homoserine lactones as chemical probes for the elucidation of plant–microbe interactions
  作者：Heike Thomanek、Sebastian T. Schenk、Elke Stein、Karl-Heinz Kogel、Adam Schikora、Wolfgang Maison

  DOI：10.1039/c3ob41215f

  日期：——

  Gram-negative bacteria often use N-acyl-homoserine lactones (AHLs) as signal molecules to monitor their local population densities and to regulate gene-expression in a process called “Quorum Sensing” (QS). This cell-to-cell communication allows bacteria to adapt to environmental changes and to behave as multicellular communities. QS plays a key role in both bacterial virulence towards the host and symbiotic interactions with other organisms. Plants also perceive AHLs and respond to them with changes in gene expression or modifications in development. Herein, we report the synthesis of new AHL-derivatives for the investigation and identification of AHL-interacting proteins. We show that our new compounds are still recognised by different bacteria and that a novel biotin-tagged-AHL derivative interacts with a bacterial AHL receptor.

  革兰氏阴性细菌常利用N-酰基高丝氨酸内酯（AHLs）作为信号分子，监测其局部种群密度，并通过一种称为“群体感应”（Quorum Sensing，简称QS）的过程调控基因表达。这种细胞间通讯使细菌能适应环境变化，表现为多细胞社群行为。QS在细菌对宿主的毒力以及其他生物的共生相互作用中发挥关键作用。植物也能感知AHLs，并以基因表达变化或发育改变来响应它们。在此，我们报道了新型AHL衍生物的合成，用于调查和鉴定AHL相互作用蛋白。我们展示，我们的新化合物仍被不同细菌识别，且一种新型生物素标记的AHL衍生物能与细菌的AHL受体相互作用。
• Synthesis of [guanido-¹³C]-γ-hydroxyarginine
  作者：Goo Yoon、T. Mark Zabriskie、Seung Hoon Cheon

  DOI：10.1002/jlcr.1570

  日期：2009.2

  This report describes an efficient method of synthesizing [guanido-13C]-γ-hydroxyarginine HCl salt. Iodolactonization of N-Boc-protected allylglycine mainly provided the cis iodo compound 2. This was converted to an amine through azide 4. The amine 5 was reacted with N-Boc-protected [13C]thiourea to afford N-Boc-protected [13C]guanidine 6, which underwent base catalyzed ring opening. Removal of the N-Boc group afforded [guanido-13C]-γ-hydroxyarginine HCl salt 7 giving a 30% overall yield of the final product from N-Boc protected allylglycine 1 in five steps. Copyright © 2008 John Wiley & Sons, Ltd.

  本报告介绍了一种合成[胍基-13C]-γ-羟基精氨酸盐酸盐的有效方法。N-Boc 保护的烯丙基甘氨酸碘内酯化主要提供了顺式碘化合物 2。2 通过叠氮化物 4 转化为胺。胺 5 与 N-Boc 保护的[13C]硫脲反应，得到 N-Boc 保护的[13C]胍 6，并在碱催化下开环。去除 N-Boc 基团后，得到[胍基-13C]-γ-羟基精氨酸盐酸盐 7，通过五个步骤从 N-Boc 保护的烯丙基甘氨酸 1 得到最终产品，总产率为 30%。Copyright © 2008 John Wiley & Sons, Ltd. All Rights Reserved.