(2R,3S)-3-tert-butyldiphenylsilyloxy-1,2-(cyclohexylidenedioxy)hex-5-ene | 1197010-57-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S)-3-tert-butyldiphenylsilyloxy-1,2-(cyclohexylidenedioxy)hex-5-ene
• 英文别名: (2R,3S)-1,2-O-cyclohexylidene-3-(tert-butyldiphenylsilyloxy)-5-hexene 3；tert-butyl-[(1S)-1-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]but-3-enoxy]-diphenylsilane
• CAS: 1197010-57-3
• 化学式: C₂₈H₃₈O₃Si
• 分子量: 450.693
• InChiKey: BRPIZZSXGOILIZ-IZZNHLLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.58
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3-tert-butyldiphenylsilyloxy-1,2-(cyclohexylidenedioxy)hex-5-ene 在 sodium hydride 、 二异丁基氢化铝 、 碳酸氢钠 、 臭氧 、 三乙胺 、 sodium bromide 、 锌 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 丙酮 为溶剂， 反应 2.92h， 生成 (5S,6R)-3-hydroxymethyl-5-O-tert-butyl-diphenylsilyl-6,7-O-cyclohexylidene-5,6,7-trihydroxy-hept-1-ene
  参考文献：
  名称：

  Stereodivergent Route to the Carbocyclic Core of 2′,3′-Olefinic Carbanucleosides: Toward the Synthesis of (l)-(+)- and (d)-(−)-Carbovir

  摘要：

  (R)-2,3-Cyclohexylideneglyceraldehyde (1) has been elegantly exploited for a stereodivergent construction of the potential precursors (ha and 11b) of (L)-(+)- and (D)-(-)-carbovirs, respectively. The key steps in this approach were Luche's allylation of formaldehyde with allylic bromide 4c to produce 5 and ring-closing metathesis of 10b using Grubbs' first-generation catalyst to obtain 11. The moderate stereoselectivity of Luche's allylation reaction resulted in attaining stereodivergence in this approach which could be realized finally through easy chromatographic separation of the two isomers of the metathesis product to obtain homochiral precursors ha and lib in good amounts.

  DOI：

  10.1021/jo200670v
• 作为产物：
  描述：

  (R)-1,4-二氧杂螺[4,5]癸烷-2-甲醛 在 咪唑 、 氯化铵 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 (2R,3S)-3-tert-butyldiphenylsilyloxy-1,2-(cyclohexylidenedioxy)hex-5-ene
  参考文献：
  名称：

  Stereoselective total synthesis of a novel regiomer of herbarumin I and its cytotoxic and antimicrobial activities

  摘要：

  Stereoselective synthesis of a novel regiomer of the natural nonenolide, herbarumin I has been accomplished. The synthesis involves the coupling of the alcohol and acid fragments of the molecule using Yamaguchi protocol followed by intramolecular ring closing metathesis. The cytotoxic and antimicrobial properties of the synthetic regiomer have been studied. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.11.010

文献信息

• A simple entry into 1,3-diols from (R)-2,3-cyclohexylideneglyceraldehyde: synthesis of (−)-galantinic acid
  作者：Bhaskar Dhotare、Angshuman Chattopadhyay

  DOI：10.1016/j.tetasy.2009.07.030

  日期：2009.9

  Aldehydes 5, 7, and 9 derived from easily accessible (R)-2,3-cyclohexylideneglyceraldehyde 1 were used as novel substrates to obtain both syn- and anti-1,3-diols in several individual reactions by subjecting each of them to some practically viable metal-mediated Barbier-type allylations under moist conditions. In this regard, a detailed investigation was made regarding the compatibility and stereoselectivity

  醛5，7和9从容易获得（派生- [R）-2,3- cyclohexylideneglyceraldehyde 1被用作新底物，以获得这两个顺式和-抗由它们中的每经受一些在多个单独的反应-1,3-二醇在潮湿条件下几乎可行的金属介导的Barbier型烯丙基化。在这方面，对与这些醛5-7的四个这种金属介导的烯丙基化相关的相容性和立体选择性进行了详细的研究。。在几个成功的反应中具有良好的收率，具有适度的选择性，并且可以容易地色谱分离产物的非对映异构体，已成功地分离出两对对映体纯的syn -1,3和抗-1,3-二醇（6a和6b；10a和10b） ）。最后，图10b已经被利用来合成（ - ） - galantinic酸甲。
• First asymmetric synthesis of the oxylipin, (6S,9R,10S)-6,9,10-trihydroxyoctadeca-7E-enoic acid
  作者：Sucheta Chatterjee、Seema V. Kanojia、Subrata Chattopadhyay、Anubha Sharma

  DOI：10.1016/j.tetasy.2011.02.008

  日期：2011.2

  A brief and facile synthesis of the title compound has been developed using cyclohexylideneglyceraldehyde as a chiral template. The key steps in the synthesis were: (i) two highly diastereoselective organometallic addition reactions to the aldehyde to furnish the required synthons with the appropriate stereogenic centers, and (ii) their cross metathesis to give the E-olefin geometry of the target compound. (C) 2011 Elsevier Ltd. All rights reserved.
• Stereoselective total synthesis of a novel regiomer of herbarumin I and its cytotoxic and antimicrobial activities
  作者：Paramesh Jangili、Jajula Kashanna、C. Ganesh Kumar、Y. Poornachandra、Biswanath Das

  DOI：10.1016/j.bmcl.2013.11.010

  日期：2014.1

  Stereoselective synthesis of a novel regiomer of the natural nonenolide, herbarumin I has been accomplished. The synthesis involves the coupling of the alcohol and acid fragments of the molecule using Yamaguchi protocol followed by intramolecular ring closing metathesis. The cytotoxic and antimicrobial properties of the synthetic regiomer have been studied. (C) 2013 Elsevier Ltd. All rights reserved.
• Stereodivergent Route to the Carbocyclic Core of 2′,3′-Olefinic Carbanucleosides: Toward the Synthesis of (<scp>l</scp>)-(+)- and (<scp>d</scp>)-(−)-Carbovir
  作者：Angshuman Chattopadhyay、Sibanarayan Tripathy

  DOI：10.1021/jo200670v

  日期：2011.7.15

  (R)-2,3-Cyclohexylideneglyceraldehyde (1) has been elegantly exploited for a stereodivergent construction of the potential precursors (ha and 11b) of (L)-(+)- and (D)-(-)-carbovirs, respectively. The key steps in this approach were Luche's allylation of formaldehyde with allylic bromide 4c to produce 5 and ring-closing metathesis of 10b using Grubbs' first-generation catalyst to obtain 11. The moderate stereoselectivity of Luche's allylation reaction resulted in attaining stereodivergence in this approach which could be realized finally through easy chromatographic separation of the two isomers of the metathesis product to obtain homochiral precursors ha and lib in good amounts.