(R)-5-[[dimethyl(1,1-dimethylethyl)-silyl]oxy]-2-pentanol | 1392409-20-9

• 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: (R)-5-[[dimethyl(1,1-dimethylethyl)-silyl]oxy]-2-pentanol
• 英文别名: (R)-1-(tert-butyldimethylsilyloxy)-pentan-4-ol；(2R)-5-[tert-butyl(dimethyl)silyl]oxypentan-2-ol
• CAS: 1392409-20-9
• 化学式: C₁₁H₂₆O₂Si
• 分子量: 218.412
• InChiKey: GAAOKOSJNUIMRV-SNVBAGLBSA-N

物化性质

• 沸点：
  245.0±23.0 °C(predicted)
• 密度：
  0.873±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.17
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-5-[[dimethyl(1,1-dimethylethyl)-silyl]oxy]-2-pentanol 在 咪唑 、 甲醇 、 4-甲基苯磺酸吡啶 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 (3RS,6R)-6-tert-butyldiphenylsilyloxyhept-1-en-3-ol
  参考文献：
  名称：

  Chemoenzymatic total synthesis of stagonolide-E

  摘要：

  Asymmetric total synthesis of small ring macrolide stagonolide-E has been described in this communication. The main highlight of our synthetic strategy is the application of ME-DKR (metal enzyme combo dynamic kinetic resolution) reaction, asymmetric reduction with Noyori's BINAL-H reagent system, stereoselective cross metathesis, and RCM (ring closing metathesis) reaction at a late stage enables us to achieve the synthesis of the target molecule in an efficient way. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.059
• 作为产物：
  描述：

  1,4-戊二醇 在 甲醇 、 chlorodicarbonyl(1-(isopropylamino)-2,3,4,5-tetraphenylcyclopentadienyl) ruthenium (II) 、 Candida antarctica CAL-B lipase 、 potassium tert-butylate 、 sodium hydride 、 potassium carbonate 作用下， 反应 7.0h， 生成 (R)-5-[[dimethyl(1,1-dimethylethyl)-silyl]oxy]-2-pentanol
  参考文献：
  名称：

  Chemoenzymatic total synthesis of stagonolide-E

  摘要：

  Asymmetric total synthesis of small ring macrolide stagonolide-E has been described in this communication. The main highlight of our synthetic strategy is the application of ME-DKR (metal enzyme combo dynamic kinetic resolution) reaction, asymmetric reduction with Noyori's BINAL-H reagent system, stereoselective cross metathesis, and RCM (ring closing metathesis) reaction at a late stage enables us to achieve the synthesis of the target molecule in an efficient way. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.059

文献信息

• Convergent Syntheses of 3,6-Dihydroxydec-4-enolides
  作者：Jonathan C. Killen、Lorraine C. Axford、Sarah E. Newberry、Thomas J. Simpson、Christine L. Willis

  DOI：10.1021/ol3018566

  日期：2012.8.17

  The total syntheses of the 3,6-dihydroxydecanolide from Cordyceps militaris and the novel C-3 epimer are reported using a diastereoselective Nozaki–Hiyama–Kishi reaction in the key cyclization to generate the 6R stereocenter.

  据报道，在关键环化反应中使用非对映选择性Nozaki–Hiyama–Kishi反应，从虫草和新的C-3差向异构体中合成了3,6-二羟基癸醇化物，以生成6 R立体中心。
• Nitrogen-appended N-alkylsulfonamides as inhibitors of γ-secretase
  作者：Carl P. Bergstrom、Charles P. Sloan、Henry H. Wang、Michael F. Parker、David W. Smith、Ming Zheng、Steven B. Hansel、Craig T. Polson、Lauren E. Barber、Isia Bursuker、Valerie L. Guss、Jason A. Corsa、Donna M. Barten、Kevin M. Felsenstein、Susan B. Roberts

  DOI：10.1016/j.bmcl.2007.10.105

  日期：2008.1

  The synthesis and gamma-secretase inhibition data for a series of nitrogen-appended N-alkylsulfonamides (11-47) are described. Inhibition of brain A beta in transgenic mice was demonstrated by two of these compounds (23 and 44). (C) 2007 Elsevier Ltd. All rights reserved.
• Chemoenzymatic total synthesis of stagonolide-E
  作者：Tapas Das、Samik Nanda

  DOI：10.1016/j.tetlet.2011.11.059

  日期：2012.1

  Asymmetric total synthesis of small ring macrolide stagonolide-E has been described in this communication. The main highlight of our synthetic strategy is the application of ME-DKR (metal enzyme combo dynamic kinetic resolution) reaction, asymmetric reduction with Noyori's BINAL-H reagent system, stereoselective cross metathesis, and RCM (ring closing metathesis) reaction at a late stage enables us to achieve the synthesis of the target molecule in an efficient way. (C) 2011 Elsevier Ltd. All rights reserved.