(2R)-N-[3,3-dimethyl-4,4-bis(trimethylsilyloxy)cyclobutanecarbonyl]-bornane-10,2-sultam | 864914-95-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2R)-N-[3,3-dimethyl-4,4-bis(trimethylsilyloxy)cyclobutanecarbonyl]-bornane-10,2-sultam
• 英文别名: [(1R)-3,3-dimethyl-2,2-bis(trimethylsilyloxy)cyclobutyl]-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]methanone；[(1R)-3,3-dimethyl-2,2-bis(trimethylsilyloxy)cyclobutyl]-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]methanone
• CAS: 864914-95-4
• 化学式: C₂₃H₄₃NO₅SSi₂
• 分子量: 501.835
• InChiKey: SXASIYPUNZQCFE-WYADAEROSA-N

物化性质

• 沸点：
  495.7±55.0 °C(predicted)
• 密度：
  1.14±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  81.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R)-N-[3,3-dimethyl-4,4-bis(trimethylsilyloxy)cyclobutanecarbonyl]-bornane-10,2-sultam 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 4-甲基苯磺酸吡啶 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 Toluene-4-sulfonic acid (1S,2R)-2-(2-ethoxy-ethoxy)-3,3-dimethyl-cyclobutylmethyl ester
  参考文献：
  名称：

  Synthetic studies of pestalotiopsin A: asymmetric synthesis of the 2-oxabicyclo[3.2.0]heptane substructure

  摘要：

  A functionalized 2-oxabicyclo [3.2.0]heptan-3-one derivative, possessing all the skeletal carbons of pestalotiopsin A, has been synthesized. For the preparation of intermediary cyclobutane derivatives in enantioenriched form, the Lewis acid-catalyzed [2+2] cycloaddition of N-propiolated Oppoizer's camphorsultam with dimethylketene bis(trimethylsilyl) acetal followed by a stereo-selective 1,4-hydride addition/protonation, has been developed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.133
• 作为产物：
  描述：

  双三甲基硅基二甲基烯酮乙醛 在 氯化锆(IV) 、 L-Selectride 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 (2R)-N-[3,3-dimethyl-4,4-bis(trimethylsilyloxy)cyclobutanecarbonyl]-bornane-10,2-sultam
  参考文献：
  名称：

  Synthetic studies of pestalotiopsin A: asymmetric synthesis of the 2-oxabicyclo[3.2.0]heptane substructure

  摘要：

  A functionalized 2-oxabicyclo [3.2.0]heptan-3-one derivative, possessing all the skeletal carbons of pestalotiopsin A, has been synthesized. For the preparation of intermediary cyclobutane derivatives in enantioenriched form, the Lewis acid-catalyzed [2+2] cycloaddition of N-propiolated Oppoizer's camphorsultam with dimethylketene bis(trimethylsilyl) acetal followed by a stereo-selective 1,4-hydride addition/protonation, has been developed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.133

文献信息

• Total Syntheses of (+)- and (−)-Pestalotiopsin A
  作者：Ken-ichi Takao、Nobuhiko Hayakawa、Reo Yamada、Taro Yamaguchi、Hiroshi Saegusa、Masatoshi Uchida、Suguru Samejima、Kin-ichi Tadano

  DOI：10.1021/jo9012546

  日期：2009.9.4

  An enantioselective total synthesis of both enantiomers of caryophyllene-type sesquiterpenoid pestalotiopsin A has been achieved, thereby establishing the absolute stereochemistry of natural (+)-pestalotiopsin A. Highlights of the synthesis include a [2 + 2] cycloaddition of N-propioloyl Oppolzer’s camphorsultam and ketene dialkyl acetal and subsequent highly stereoselective 1,4-hydride addition/protonation

  一个对映体的全合成的叶绿素型倍半萜类香蒜素A的对映体已经实现，从而建立了天然（+）-脂蛋白A的绝对立体化学。该合成的重点包括N-丙炔基Oppolzer樟脑的[2 + 2]环加成。乙烯酮二烷基乙缩醛，随后的高立体选择性1,4-氢化物加成/质子化，功能化的双环内酯与醛的醛醇缩合反应，高效的分子内Nozaki-Hiyama-Kishi（NHK）反应，用于构建高应变（E）-环壬烯环，以及钯催化的烯丙基甲磺酸酯的还原，同时保留了E构型。
• Synthetic studies of pestalotiopsin A: asymmetric synthesis of the 2-oxabicyclo[3.2.0]heptane substructure
  作者：Ken-ichi Takao、Hiroshi Saegusa、Tomohiro Tsujita、Takenori Washizawa、Kin-ichi Tadano

  DOI：10.1016/j.tetlet.2005.06.133

  日期：2005.8

  A functionalized 2-oxabicyclo [3.2.0]heptan-3-one derivative, possessing all the skeletal carbons of pestalotiopsin A, has been synthesized. For the preparation of intermediary cyclobutane derivatives in enantioenriched form, the Lewis acid-catalyzed [2+2] cycloaddition of N-propiolated Oppoizer's camphorsultam with dimethylketene bis(trimethylsilyl) acetal followed by a stereo-selective 1,4-hydride addition/protonation, has been developed. (c) 2005 Elsevier Ltd. All rights reserved.