(3RS,6R)-6-tert-butyldiphenylsilyloxyhept-1-en-3-ol | 1353998-66-9

• 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: (3RS,6R)-6-tert-butyldiphenylsilyloxyhept-1-en-3-ol
• 英文别名: (6R)-6-[tert-butyl(diphenyl)silyl]oxyhept-1-en-3-ol
• CAS: 1353998-66-9
• 化学式: C₂₃H₃₂O₂Si
• 分子量: 368.591
• InChiKey: YBUCJJTZIRUHPV-FIWHBWSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.28
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 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：

  (3RS,6R)-6-tert-butyldiphenylsilyloxyhept-1-en-3-ol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以90%的产率得到(6R)-6-[tert-butyl(diphenyl)silyl]oxyhept-1-en-3-one
  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 咪唑 、 甲醇 、 chlorodicarbonyl(1-(isopropylamino)-2,3,4,5-tetraphenylcyclopentadienyl) ruthenium (II) 、 Candida antarctica CAL-B lipase 、 potassium tert-butylate 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 potassium carbonate 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.0h， 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

文献信息

• A Chemoenzymatic Synthesis of Hept-6-ene-2,5-diol Stereomers: Application to Asymmetric Synthesis of Decarestrictine L, Pyrenophorol, and Stagonolide E
  作者：Sucheta Chatterjee、Sneha Ghadigaonkar、Payel Sur、Anubha Sharma、Subrata Chattopadhyay

  DOI：10.1021/jo5012575

  日期：2014.9.5

  The stereomers of hept-6-ene-2,5-diol derivatives were conceived as useful chiral intermediates and were synthesized starting from sulcatol using two lipase-catalyzed acylation reactions as the key steps. The versatility of the intermediates was demonstrated by converting them to the titled tetrahydropyran, macrolide, and macrodiolide compounds using standard synthetic protocols.
• 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.