Methyl 3-[tert-butyl(dimethyl)silyl]oxy-2-(phenylmethoxycarbonylamino)propanoate | 957208-94-5

• 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: Methyl 3-[tert-butyl(dimethyl)silyl]oxy-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 957208-94-5
• 化学式: C₁₈H₂₉NO₅Si
• 分子量: 367.517
• InChiKey: MGMBDAZINVGJIJ-UHFFFAOYSA-N

物化性质

• 沸点：
  434.8±45.0 °C(Predicted)
• 密度：
  1.063±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.48
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 3-[tert-butyl(dimethyl)silyl]oxy-2-(phenylmethoxycarbonylamino)propanoate 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 N-benzyloxycarbonyl-O-dimethyl-butylsilyl-DL-serine
  参考文献：
  名称：

  N-羟基酰胺合成中温和有效的路易斯酸促进的三苯甲基化反应：（-）-Cobactin T的简便合成

  摘要：

  描述了有效的，高产率的路易斯酸促进的O-三苯甲基羟胺衍生物的脱保护。在这些温和条件下，可以耐受一系列酸不稳定的保护基，例如N -Boc和O -TBS。本方法适用于广泛的羟胺衍生物的合成，包括通常表现出显着生物学活性的N-羟基酰胺（异羟肟酸），N-羟基磺酰胺和N-羟基脲。还演示了该方法在简明合成（-）-Cobactin T（18）中的应用。

  DOI：

  10.1021/jo701411d
• 作为产物：
  描述：

  氯甲酸苄酯 在 咪唑 、 sodium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 Methyl 3-[tert-butyl(dimethyl)silyl]oxy-2-(phenylmethoxycarbonylamino)propanoate
  参考文献：
  名称：

  An innovative strategy for the synthesis of a new series of potent aminopeptidase (APN or CD13) inhibitors derived from the oxepin-4-one family

  摘要：

  Derivatives from the aminobenzosuberone family have been recently synthesized and recognized as highly selective inhibitors of aminopeptidase N (APN)/CD13 (EC 3.4.11.2), an important target for cell migration processes involved in particular in tumor invasion. We present here a much more straightforward synthesis of analogues belonging to a novel isosteric oxo series which also possesses excellent inhibitory potential against APN. Their synthesis, as reported here, relied on an interesting iodine(III)-mediated rearrangement originally described by Koser and Justik as the key step. This represents the second application of this rearrangement in medicinal chemistry. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2011.03.043

文献信息

• A mild and selective cleavage of tert-butyldimethylsilyl ethers by indium(III) chloride
  作者：Jhillu S. Yadav、Basi V. Subba Reddy、Chinnala Madan

  DOI：10.1039/b004937i

  日期：——

  Alkyl tert-butyldimethylsilyl ethers are selectively deprotected to the corresponding alcohols in high yields for the first time by indium(III) chloride in refluxing aqueous acetonitrile. Several functional groups like OBn, Boc, CBz, OBz, O-allyl, OTBDPS, OAc, OMe, ethers, esters and olefins present in the substrate are unaffected.

  将烷基叔丁基二甲基甲硅烷基醚选择性脱保护为相应的酒类 第一次高产 氯化铟（III） 在回流的水溶液中 乙腈。几个功能组，例如OBn，Boc，CBz，OBz，O-烯丙基，OTBDPS，OAc，OMe，醚， 酯类 和 烯烃 存在于基材中的不受影响。
• An innovative strategy for the synthesis of a new series of potent aminopeptidase (APN or CD13) inhibitors derived from the oxepin-4-one family
  作者：Lionel Roux、Cédric Charrier、Emmanuel Salomon、Meral Ilhan、Philippe Bisseret、Céline Tarnus

  DOI：10.1016/j.tetlet.2011.03.043

  日期：2011.5

  Derivatives from the aminobenzosuberone family have been recently synthesized and recognized as highly selective inhibitors of aminopeptidase N (APN)/CD13 (EC 3.4.11.2), an important target for cell migration processes involved in particular in tumor invasion. We present here a much more straightforward synthesis of analogues belonging to a novel isosteric oxo series which also possesses excellent inhibitory potential against APN. Their synthesis, as reported here, relied on an interesting iodine(III)-mediated rearrangement originally described by Koser and Justik as the key step. This represents the second application of this rearrangement in medicinal chemistry. (C) 2011 Published by Elsevier Ltd.
• Mild and Efficient Lewis Acid-Promoted Detritylation in the Synthesis of <i>N</i>-Hydroxy Amides:  A Concise Synthesis of (−)-Cobactin T
  作者：Shyh-Ming Yang、Bharat Lagu、Lawrence J. Wilson

  DOI：10.1021/jo701411d

  日期：2007.10.1

  Lewis acid promoted deprotection of O-trityl hydroxylamine derivatives is described. A range of acid-labile protecting groups, such as N-Boc and O-TBS, were tolerated under these mild conditions. The present method is applicable to the synthesis of a broad range of hydroxylamine derivatives, including N-hydroxy amides (hydroxamic acids), N-hydroxy sulfonamides, and N-hydroxy ureas, which often exhibit

  描述了有效的，高产率的路易斯酸促进的O-三苯甲基羟胺衍生物的脱保护。在这些温和条件下，可以耐受一系列酸不稳定的保护基，例如N -Boc和O -TBS。本方法适用于广泛的羟胺衍生物的合成，包括通常表现出显着生物学活性的N-羟基酰胺（异羟肟酸），N-羟基磺酰胺和N-羟基脲。还演示了该方法在简明合成（-）-Cobactin T（18）中的应用。