Tr-Ser(OBn)-Im | 1007843-08-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: Tr-Ser(OBn)-Im
• 英文别名: Tr-(L)Ser(OBn)-Im；(2S)-1-imidazol-1-yl-3-phenylmethoxy-2-(tritylamino)propan-1-one
• CAS: 1007843-08-4
• 化学式: C₃₂H₂₉N₃O₂
• 分子量: 487.601
• InChiKey: YZAFCWUYBCCWIG-PMERELPUSA-N

物化性质

• 沸点：
  636.8±65.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  56.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Tr-Ser(OBn)-Im 在 吗啉 、 四(三苯基膦)钯 、 正丁基锂 、 sodium hydride 、 lithium tri-t-butoxyaluminum hydride 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 63.0h， 生成
  参考文献：
  名称：

  Highly Stereoselective Syntheses of syn- and anti-1,2-Amino Alcohols

  摘要：

  The reduction of N-protected amino ketones can be carried stereoselectively to produce either the syn- or anti-amino alcohol diastereomer. Carbamate-protected amino ketones can be reduced predictably and selectively to anti-amino alcohols with LiAlH(O-t-BU)(3) in ethanol at -78 degreesC. N-Trityl-protected amino ketones can be reduced selectively to syn-amino alcohols with LiAlH(O-t-Bu)(3) in THF at -5 degreesC.

  DOI：

  10.1021/jo010270f
• 作为产物：
  描述：

  O-苄基-L-丝氨酸 在 三甲基氯硅烷 、 三乙胺 作用下， 以 四氢呋喃 、 氯仿 、 乙腈 为溶剂， 反应 1.0h， 生成 Tr-Ser(OBn)-Im
  参考文献：
  名称：

  Highly Stereoselective Syntheses of syn- and anti-1,2-Amino Alcohols

  摘要：

  The reduction of N-protected amino ketones can be carried stereoselectively to produce either the syn- or anti-amino alcohol diastereomer. Carbamate-protected amino ketones can be reduced predictably and selectively to anti-amino alcohols with LiAlH(O-t-BU)(3) in ethanol at -78 degreesC. N-Trityl-protected amino ketones can be reduced selectively to syn-amino alcohols with LiAlH(O-t-Bu)(3) in THF at -5 degreesC.

  DOI：

  10.1021/jo010270f

文献信息

• Enantiomerically Pure <i>trans</i>-β-Lactams from α-Amino Acids via Compact Fluorescent Light (CFL) Continuous-Flow Photolysis
  作者：Yvette S. Mimieux Vaske、Maximillian E. Mahoney、Joseph P. Konopelski、David L. Rogow、William J. McDonald

  DOI：10.1021/ja1050023

  日期：2010.8.18

  beta-lactams has been shown to vary from modest to nearly complete. An extremely facile, atom-economical method for the epimerization of the product mixture to the trans isomer, which is generally highly crystalline, has been developed. Evidence for C3 epimerization of Weinreb amide structures via a nonbasic, purely thermal route is presented. Subsequent transformations of both the Weinreb amide at C3 (beta-lactam

  来自对映体纯 (EP) α-氨基酸的 α-重氮-N-甲氧基-N-甲基 (Weinreb) β-酮酰胺的光解通过分子内 Wolff 重排提供相应的 EP β-内酰胺。通过标准紫外线照射或使用 100 W 紧凑型荧光灯可促进光化学反应；后者为标准光解条件提供了安全且环保的替代方案。由廉价的实验室设备制成的连续流光化学反应器减少了反应时间并且易于扩大规模。β-内酰胺产品的非对映选择性（顺式或反式）已显示出从适度到几乎完全的变化。已经开发出一种极其简便、原子经济的方法，用于将产物混合物差向异构化为反式异构体，该异构体通常是高度结晶的。提供了 Weinreb 酰胺结构通过非碱性纯热途径发生 C3 差向异构化的证据。C3 处的 Weinreb 酰胺（β-内酰胺编号）和 C4 处的氨基酸侧链的后续转化具有良好的耐受性，从而可以采用多种方法来构建不同的 β-内酰胺结构。该技术展示了一种常见中间体的合成，该
• Structural Characterization of an Enantiomerically Pure Amino Acid Imidazolide and Direct Formation of the β-Lactam Nucleus from an α-Amino Acid
  作者：Brian S. Gerstenberger、Jinzhen Lin、Yvette S. Mimieux、Lauren E. Brown、Allen G. Oliver、Joseph P. Konopelski

  DOI：10.1021/ol7025922

  日期：2008.2.1

  Decomposition of a diazo beta-ketoamide derived from N-trityl serine imidazolide and N-protected acetanilides provides, instead of the expected beta-acyloxindole product, an enantiomerically pure (EP) beta-lactam. The amino acid stereocenter is incorporated, the second chiral center is induced, and trityl protection of the beta-lactam ring is realized for the first time. The desired beta-acyloxindole is obtained from oxindole and Tr-Ser(OBn)-imidazole, the X-ray of which provides the first structural determination of an EP amino acid imidazolide.
• Diazonamide Support Studies: Stereoselective Formation of the C10 Chiral Center in both the CDEFG and AEFG Fragments
  作者：Jinzhen Lin、Brian S. Gerstenberger、Nhu Y T. Stessman、Joseph P. Konopelski

  DOI：10.1021/ol8014336

  日期：2008.9.18

  The synthesis of both the AEFG macrolactam and the CDEFG bis-indole/tyrosine units found in the marine natural product diazonamide A is presented. Key to the success of the synthesis is the highly stereoselective direct C-arylation of an oxindole by an aryllead(IV) reagent derived from tyrosine.
• Highly Stereoselective Syntheses of <i>s</i><i>yn-</i> and <i>a</i><i>nti</i>-1,2-Amino Alcohols
  作者：Robert V. Hoffman、Najib Maslouh、Francisco Cervantes-Lee

  DOI：10.1021/jo010270f

  日期：2002.2.1

  The reduction of N-protected amino ketones can be carried stereoselectively to produce either the syn- or anti-amino alcohol diastereomer. Carbamate-protected amino ketones can be reduced predictably and selectively to anti-amino alcohols with LiAlH(O-t-BU)(3) in ethanol at -78 degreesC. N-Trityl-protected amino ketones can be reduced selectively to syn-amino alcohols with LiAlH(O-t-Bu)(3) in THF at -5 degreesC.