tert-butyl 3-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-8,8-dimethyl-4-oxo-7,9-dioxa-1-azaspiro[4.5]decane-1-carboxylate | 1384881-36-0

• 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: tert-butyl 3-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-8,8-dimethyl-4-oxo-7,9-dioxa-1-azaspiro[4.5]decane-1-carboxylate
• CAS: 1384881-36-0
• 化学式: C₃₂H₄₅NO₆Si
• 分子量: 567.798
• InChiKey: DPOYZYVRJFYHRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.91
• 重原子数：
  40.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  74.3
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-8,8-dimethyl-4-oxo-7,9-dioxa-1-azaspiro[4.5]decane-1-carboxylate 在 sodium periodate 、 cerium(III) chloride heptahydrate 、 ruthenium(III) trichloride hydrate 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 为溶剂， 反应 43.0h， 生成 tert-butyl (3R,4R)-3-[2-[tert-butyl(diphenyl)silyl]oxyethyl]-4-hydroxy-4,8,8-trimethyl-2-oxo-7,9-dioxa-1-azaspiro[4.5]decane-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
• 作为产物：
  描述：

  (5-甲酰基-2,2-二甲基-1,3-二氧六环-5-基)氨基甲酸叔丁酯 在 正丁基锂 、 四甲基乙二胺 、 sodium cyanoborohydride 、 戴斯-马丁氧化剂 、 臭氧 、 溶剂黄146 作用下， 以 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 tert-butyl 3-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-8,8-dimethyl-4-oxo-7,9-dioxa-1-azaspiro[4.5]decane-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