(S)-tert-butyl 3-((1S,2S)-4-(tert-butyldiphenylsilyloxy)-1-hydroxy-2-(triethylsilyloxy)butyl)-2-oxopyrrolidine-1-carboxylate | 1021460-68-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (S)-tert-butyl 3-((1S,2S)-4-(tert-butyldiphenylsilyloxy)-1-hydroxy-2-(triethylsilyloxy)butyl)-2-oxopyrrolidine-1-carboxylate
• 英文别名: tert-butyl (3S)-3-[(1S,2S)-4-[tert-butyl(diphenyl)silyl]oxy-1-hydroxy-2-triethylsilyloxybutyl]-2-oxopyrrolidine-1-carboxylate
• CAS: 1021460-68-3
• 化学式: C₃₅H₅₅NO₆Si₂
• 分子量: 641.996
• InChiKey: MKDYVHDBFUIJQG-CHQNGUEUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.49
• 重原子数：
  44
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  85.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-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84%的产率得到tert-butyl 2-((3S,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
• 作为产物：
  描述：

  1-(叔丁氧羰基)-2-吡咯烷酮 、 (S)-4-(t-butyldiphenylsiloxy)-2-(triethylsiloxy)butanal 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以47%的产率得到(S)-tert-butyl 3-((1S,2S)-4-(tert-butyldiphenylsilyloxy)-1-hydroxy-2-(triethylsilyloxy)butyl)-2-oxopyrrolidine-1-carboxylate
  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.