(5S)-3-[(2R)-2-[tert-butyl(dimethyl)silyl]oxyundec-10-enyl]-5-methyl-3-phenylsulfanyloxolan-2-one | 862603-29-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (5S)-3-[(2R)-2-[tert-butyl(dimethyl)silyl]oxyundec-10-enyl]-5-methyl-3-phenylsulfanyloxolan-2-one
• CAS: 862603-29-0
• 化学式: C₂₈H₄₆O₃SSi
• 分子量: 490.823
• InChiKey: LSKSGCGBXWEAJJ-BIUYVPHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.55
• 重原子数：
  33
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5S)-3-[(2R)-2-[tert-butyl(dimethyl)silyl]oxyundec-10-enyl]-5-methyl-3-phenylsulfanyloxolan-2-one 在 Grubbs catalyst first generation 、 sodium acetate 、 对甲苯磺酰肼 作用下， 以 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 40.0h， 生成 (S)-3-((2R,13R)-2-(tert-Butyl-dimethyl-silanyloxy)-13-{(2S,5R,2'S,5'R)-5'-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-13-hydroxy-tridecyl)-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one
  参考文献：
  名称：

  Stereoselective Syntheses of Rolliniastatin 1, Rollimembrin, and Membranacin

  摘要：

  A radical cyclization of beta-alkoxyvinyl sulfoxides-Pummerer rearrangement-allylation protocol was successfully applied to the synthesis of the threo/cis/threo/cis/erythro bis-oxolane moiety in rolliniastatin 1 (1), rollimembrin (2), and membranacin (3).

  DOI：

  10.1021/ja0526867
• 作为产物：
  描述：

  8-溴-1-辛烯 在 2,6-二甲基吡啶 、 碳酸氢钠 、 magnesium 、 sodium iodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 丙酮 为溶剂， 反应 69.5h， 生成 (5S)-3-[(2R)-2-[tert-butyl(dimethyl)silyl]oxyundec-10-enyl]-5-methyl-3-phenylsulfanyloxolan-2-one
  参考文献：
  名称：

  Stereoselective Syntheses of Rolliniastatin 1, Rollimembrin, and Membranacin

  摘要：

  A radical cyclization of beta-alkoxyvinyl sulfoxides-Pummerer rearrangement-allylation protocol was successfully applied to the synthesis of the threo/cis/threo/cis/erythro bis-oxolane moiety in rolliniastatin 1 (1), rollimembrin (2), and membranacin (3).

  DOI：

  10.1021/ja0526867

文献信息

• Total synthesis of 27-hydroxy-bullatacin and its C-15 epimer, and studies on their inhibitory effect on bovine heart mitochondrial complex I functions
  作者：Zhiyong Chen、Subhash C. Sinha

  DOI：10.1016/j.tet.2007.11.089

  日期：2008.2

  The total synthesis of 27-hydroxybullatacin and its C-15 epimer has been achieved using rhenium(VII) oxides-mediated and Co(modp)(2)-catalyzed oxidative cyclization (OC), diastereoselective alkynylation, Brown's enantioselective allylboration, and Grubbs' cross metathesis as the key reactions. The inhibitory effect of these compounds on the complex I function, as determined by using bovine submitochondrial particles, was in low nanomolar range. (C) 2007 Elsevier Ltd. All rights reserved.
• Stereoselective Syntheses of Rolliniastatin 1, Rollimembrin, and Membranacin
  作者：Gyochang Keum、Cheol Hee Hwang、Soon Bang Kang、Youseung Kim、Eun Lee

  DOI：10.1021/ja0526867

  日期：2005.7.1

  A radical cyclization of beta-alkoxyvinyl sulfoxides-Pummerer rearrangement-allylation protocol was successfully applied to the synthesis of the threo/cis/threo/cis/erythro bis-oxolane moiety in rolliniastatin 1 (1), rollimembrin (2), and membranacin (3).