(R)-4-tert-butyldiphenylsilyloxypentanal | 1307273-43-3

• 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)-4-tert-butyldiphenylsilyloxypentanal
• 英文别名: (4R)-4-[tert-butyl(diphenyl)silyl]oxypentanal
• CAS: 1307273-43-3
• 化学式: C₂₁H₂₈O₂Si
• 分子量: 340.538
• InChiKey: SSKDJDUYVQNBRB-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-4-tert-butyldiphenylsilyloxypentanal 在 lithium aluminium tetrahydride 、 草酰氯 、 (R)-1,1'-Bi-2-naphthol 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 (3R,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 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 二氯甲烷 为溶剂， 反应 15.0h， 生成 (R)-4-tert-butyldiphenylsilyloxypentanal
  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

• An Efficient Convergent Access to Spiroketal Segment of (+)-Spiroxaline Methyl Ether
  作者：Narshinha Argade、Mandeep Singh

  DOI：10.1055/s-0030-1258456

  日期：2011.4

  Starting from trimethylsilylacetylene, a facile synthesis of optically pure spiroketal unit of (+)-spiroxaline methyl ether has been described. The synthesis entails stepwise alkylation and acylation of an alkyne with two different readily available chiral building blocks followed by the reductive in situ regio- and stereoselective spiroketalization pathway. alkyne - (R)-oxirane - (R)-γ-valerolactone

  从三甲基甲硅烷基乙炔开始，已经描述了容易合成光学纯的（+）-螺氧杂环林甲基醚的螺酮基单元。合成需要使用两个易于获得的手性结构单元逐步进行炔烃的烷基化和酰化，然后进行还原性原位区域和立体选择性螺酮缩合途径。 炔烃-（R）-环氧乙烷-（R）-γ-戊内酯-亲核反应-（+）-螺段合成
• 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.
• 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.