tert-butyl 2-((3R,4S,5S)-5-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-hydroxy-2-oxotetrahydrofuran-3-yl)ethylcarbamate | 1021460-69-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: tert-butyl 2-((3R,4S,5S)-5-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-hydroxy-2-oxotetrahydrofuran-3-yl)ethylcarbamate
• 英文别名: tert-butyl N-[2-[(3R,4S,5S)-5-[2-[tert-butyl(diphenyl)silyl]oxyethyl]-4-hydroxy-2-oxooxolan-3-yl]ethyl]carbamate
• CAS: 1021460-69-4
• 化学式: C₂₉H₄₁NO₆Si
• 分子量: 527.733
• InChiKey: WFBLKJRYBWKADK-DSITVLBTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  94.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (R)-tert-butyl 3-((1S,2S)-4-(tert-butyldiphenylsilyloxy)-1-hydroxy-2-(triethylsilyloxy)butyl)-2-oxopyrrolidine-1-carboxylate 在 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以90%的产率得到tert-butyl 2-((3R,4S,5S)-5-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-hydroxy-2-oxotetrahydrofuran-3-yl)ethylcarbamate
  参考文献：
  名称：

  An acid-catalyzed ring-switch reaction of lactams to lactones: concise synthesis of 2,4-dialkyl-3-hydroxybutanolides

  摘要：

  A novel approach for the synthesis of 2,4-dialkyl-3-hydroxybutanolides, having three successive stereogenic centers, by an acid-catalyzed ring-switch reaction of 2-(2-hydroxyalkyl)lactams is described. This transformation was applied to the synthesis of the key intermediates of teromerase inhibitor UCS1025A. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.107

文献信息

• An acid-catalyzed ring-switch reaction of lactams to lactones: concise synthesis of 2,4-dialkyl-3-hydroxybutanolides
  作者：Chiaki Yamauchi、Masami Kuriyama、Rumiko Shimazawa、Tsumoru Morimoto、Kiyomi Kakiuchi、Ryuichi Shirai

  DOI：10.1016/j.tet.2008.01.107

  日期：2008.3

  A novel approach for the synthesis of 2,4-dialkyl-3-hydroxybutanolides, having three successive stereogenic centers, by an acid-catalyzed ring-switch reaction of 2-(2-hydroxyalkyl)lactams is described. This transformation was applied to the synthesis of the key intermediates of teromerase inhibitor UCS1025A. (c) 2008 Elsevier Ltd. All rights reserved.