(2R)-2-[(tert-butyldimethylsilyl)oxy]-1-[(2R)-oxiran-2-yl]pentadecane | 1202063-96-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2R)-2-[(tert-butyldimethylsilyl)oxy]-1-[(2R)-oxiran-2-yl]pentadecane
• 英文别名: tert-butyl-dimethyl-[(2R)-1-[(2R)-oxiran-2-yl]pentadecan-2-yl]oxysilane
• CAS: 1202063-96-4
• 化学式: C₂₃H₄₈O₂Si
• 分子量: 384.718
• InChiKey: XXVFGXZBEWPQAB-FGZHOGPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.87
• 重原子数：
  26
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-二噻烷 、 (2R)-2-[(tert-butyldimethylsilyl)oxy]-1-[(2R)-oxiran-2-yl]pentadecane 在 正丁基锂 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 1.0h， 以86%的产率得到(2R,4R)-4-[tert-butyl(dimethyl)silyl]oxy-1-(1,3-dithian-2-yl)heptadecan-2-ol
  参考文献：
  名称：

  Stereoselective synthesis of bioactive natural spiroacetals aculeatins A and B

  摘要：

  The stereoselective synthesis of two naturally occurring bioactive spiroacetals, aculeatins A and B has been accomplished using 1-tetradecanal as the starting material. The sequence introduces diastereoselective iodine-induced electrophilic cyclization and ring opening of epoxide with 1,3-dithiane as the key steps. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.162
• 作为产物：
  描述：

  在 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 (2R)-2-[(tert-butyldimethylsilyl)oxy]-1-[(2R)-oxiran-2-yl]pentadecane
  参考文献：
  名称：

  Synthesis of Aculeatins A and B via Iterative Hydrolytic Kinetic Resolution

  摘要：

  A simple and concise approach for the synthesis of aculeatins A and B starting from (+/-)-epichlorohydrin is described. The synthetic strategy features Jacobsen's hydrolytic kinetic resolution and a Linchpin coupling as key steps.

  DOI：

  10.1055/s-0029-1218687

文献信息

• Anticancer Agents from the Australian Tropical Rainforest: Spiroacetals EBC-23, 24, 25, 72, 73, 75 and 76
  作者：Lin Dong、Heiko Schill、Rebecca L. Grange、Achim Porzelle、Jenny P. Johns、Peter G. Parsons、Victoria A. Gordon、Paul W. Reddell、Craig M. Williams

  DOI：10.1002/chem.200901525

  日期：2009.10.26

  EBC‐23, 24, 25, 72, 73, 75 and 76 were isolated from the fruit of Cinnamomum laubatii (family Lauraceae) in the Australian tropical rainforests. EBC‐23 (1) was synthesized stereoselectively, in nine linear steps in 8 % overall yield, to confirm the reported relative stereochemistry and determine the absolute stereochemistry. Key to the total synthesis was a series of Tietze–Smith linchpin reactions

  EBC-23、24、25、72、73、75和76是从澳大利亚热带雨林中的laubatii肉桂（月桂科）的果实中分离出来的。EBC-23（1）以9个线性步骤立体选择性合成，总产率为8％，以确认报道的相对立体化学并确定绝对立体化学。全面合成的关键是一系列的Tietze–Smith linchpin反应。发现新的螺缩醛结构基序，例如EBC-23（1），可在小鼠模型中抑制雄激素非依赖性前列腺肿瘤细胞DU145的生长，表明其具有治疗成人难治性实体瘤的潜力。
• Synthesis of Aculeatins A and B via Iterative Hydrolytic Kinetic Resolution
  作者：Pradeep Kumar、Anand Harbindu

  DOI：10.1055/s-0029-1218687

  日期：2010.5

  A simple and concise approach for the synthesis of aculeatins A and B starting from (+/-)-epichlorohydrin is described. The synthetic strategy features Jacobsen's hydrolytic kinetic resolution and a Linchpin coupling as key steps.
• Stereoselective synthesis of bioactive natural spiroacetals aculeatins A and B
  作者：Biswanath Das、Martha Krishnaiah、Chithaluri Sudhakar

  DOI：10.1016/j.bmcl.2010.01.162

  日期：2010.4

  The stereoselective synthesis of two naturally occurring bioactive spiroacetals, aculeatins A and B has been accomplished using 1-tetradecanal as the starting material. The sequence introduces diastereoselective iodine-induced electrophilic cyclization and ring opening of epoxide with 1,3-dithiane as the key steps. (C) 2010 Elsevier Ltd. All rights reserved.