(Z)-4-(5-((tert-butoxycarbonyl)amino)-2,2-dimethyl-1,3-dioxane-5-carbonyl)-6-((tert-butyldiphenylsilyl)oxy)hex-2-en-2-yl diisopropylcarbamate | 1384881-45-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-4-(5-((tert-butoxycarbonyl)amino)-2,2-dimethyl-1,3-dioxane-5-carbonyl)-6-((tert-butyldiphenylsilyl)oxy)hex-2-en-2-yl diisopropylcarbamate
• CAS: 1384881-45-1
• 化学式: C₄₁H₆₂N₂O₈Si
• 分子量: 739.037
• InChiKey: JHVJWJOUKSMHPW-ZXPTYKNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.34
• 重原子数：
  52.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  112.63
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (Z)-4-(5-((tert-butoxycarbonyl)amino)-2,2-dimethyl-1,3-dioxane-5-carbonyl)-6-((tert-butyldiphenylsilyl)oxy)hex-2-en-2-yl diisopropylcarbamate 在 cerium(III) chloride heptahydrate 、 臭氧 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.5h， 生成
  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 、 戴斯-马丁氧化剂 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (Z)-4-(5-((tert-butoxycarbonyl)amino)-2,2-dimethyl-1,3-dioxane-5-carbonyl)-6-((tert-butyldiphenylsilyl)oxy)hex-2-en-2-yl diisopropylcarbamate
  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