tert-butyl 4-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-2,2-bis(hydroxymethyl)-3-oxopyrrolidine-1-carboxylate | 1384881-41-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: tert-butyl 4-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-2,2-bis(hydroxymethyl)-3-oxopyrrolidine-1-carboxylate
• CAS: 1384881-41-7
• 化学式: C₁₃H₂₅NO₅
• 分子量: 275.345
• InChiKey: HABNECTWFNENPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.41
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  77.02
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-2,2-bis(hydroxymethyl)-3-oxopyrrolidine-1-carboxylate 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以97%的产率得到tert-butyl N-(5-acetyl-2,2-dimethyl-1,3-dioxan-5-yl)carbamate
  参考文献：
  名称：

  Stereoselective functionalization of pyrrolidinone moiety towards the synthesis of salinosporamide A

  摘要：

  An important feature of the synthesis of salinosporamide A. a potent proteasome inhibitor, is the establishment of the quaternary stereocenter at C3. A new route has been developed based on the methylation of a functionalized pyrrolidinone. Direct methylation reaction led to the unwanted diastereomer: however, by means of a Corey-Chaykovsky reaction followed by LiAlH4 epoxide opening, the desired alcohol was obtained. The pyrrolidinone was elaborated through a key allylation reaction between a tertiary allyltitanium reagent and an aldehyde bearing a spiroketal moiety in alpha-position. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.05.103
• 作为产物：
  描述：

  n-[2-羟基-1,1-双(羟基甲基)-乙基]氨基甲酸叔丁酯 在 草酰氯 、 cerium(III) chloride heptahydrate 、 对甲苯磺酸 、 二甲基亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 tert-butyl 4-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-2,2-bis(hydroxymethyl)-3-oxopyrrolidine-1-carboxylate
  参考文献：
  名称：

  Stereoselective functionalization of pyrrolidinone moiety towards the synthesis of salinosporamide A

  摘要：

  An important feature of the synthesis of salinosporamide A. a potent proteasome inhibitor, is the establishment of the quaternary stereocenter at C3. A new route has been developed based on the methylation of a functionalized pyrrolidinone. Direct methylation reaction led to the unwanted diastereomer: however, by means of a Corey-Chaykovsky reaction followed by LiAlH4 epoxide opening, the desired alcohol was obtained. The pyrrolidinone was elaborated through a key allylation reaction between a tertiary allyltitanium reagent and an aldehyde bearing a spiroketal moiety in alpha-position. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.05.103