(3R,4S)-4-(methoxymethoxy)-2,2-dimethyl-6-trimethylsilylhex-5-yn-3-ol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4S)-4-(methoxymethoxy)-2,2-dimethyl-6-trimethylsilylhex-5-yn-3-ol
• 化学式: C₁₃H₂₆O₃Si
• 分子量: 258.433
• InChiKey: OPEAWIGCAIBCGM-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.26
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  特戊醛 、 [3-(methoxymethoxy)-3-(tributylstannyl)-1-propynyl]trimethylsilane 在 丁基三氯化锡 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到(3R,4S)-4-(methoxymethoxy)-2,2-dimethyl-6-trimethylsilylhex-5-yn-3-ol
  参考文献：
  名称：

  Highly Diastereoselective Synthesis of Propargylic 1,2-anti-Diol Derivatives Using α-Alkoxypropargylstannanes

  摘要：

  [GRAPHICS]Propargylic 1,2-anti-diol derivatives 2 and 10 are prepared in high yield and excellent diastereoselectivity by addition of alpha -alkoxypropargyl-stannanes 4a and 4b to aldehydes in the presence of BuSnCl3. We also introduce the use of KF on Celite as a convenient and mild reagent for removal of the organotin waste products of these reactions.

  DOI：

  10.1021/ol016536m

文献信息

• Addition of Hetero Allenyl Copper Reagents to Aldehydes: Scope and Behavior
  作者：Emmanuel Vrancken、Nacira Alouane、Hélène Gérard、Pierre Mangeney

  DOI：10.1021/jo062344z

  日期：2007.3.1

  propargylic amines or ethers react with aldehydes to give regioselectively the corresponding anti-homopropargylic alcohols with a high level of diastereoselectivity. Such selectivity could be obtained independently of the nature of the heteroatom (amine or ethers) or the acetylenic substituents. Excellent selectivities can be reached regardless of the aldehydes used, remarkably also with vinylic or acetylenic

  衍生自炔丙基胺或醚的氰基丙酸酯与醛反应，以区域选择性地产生具有高非对映选择性的相应的抗同炔丙基醇。可以独立于杂原子（胺或醚）或炔属取代基的性质而获得这种选择性。无论使用哪种醛，都能达到极好的选择性，尤其对于乙烯基或炔属的醛。带有不同炔基取代基的铜酸盐的反应活性等级被确定为：SiMe 3> Ph>等 还发现在HMPA的存在下加成至醛的反应速率减慢，这突出了Li抗衡离子的关键作用。DFT计算表明，与不稳定的炔丙基异构体相比，速率和炔属取代基之间的关系与可能的金属向平衡无关，而与反应性烯丙基种类的稳定性有关。
• Preparation of <i>anti</i>-1,2-Disubstituted Homopropargylic Alcohols by Addition of Allenyl(cyano)cuprates to Aldehydes
  作者：Emmanuel Vrancken、Pierre Mangeney、Nacira Alouane

  DOI：10.1055/s-2007-965969

  日期：2007.4

  The generality of the addition of allenyl(cyano)cuprates to aldehydes to afford anti-1,2-disubstituted homopropargylic alcohols was studied. The reaction is general, regardless of the nature of the cyanocuprate, although with alkyl-substituted derivatives the anti selectivity is dependent upon the nature of the aldehyde.

  研究了烯丙基（氰基）铜酸盐与醛加成生成反-1,2-二取代均丙炔醇的通用性。尽管烷基取代衍生物的反选择性取决于醛的性质，但无论氰基杯酸盐的性质如何，反应都是一般的。
• Highly Diastereoselective Synthesis of Propargylic 1,2-<i>a</i><i>nti</i>-Diol Derivatives Using α-Alkoxypropargylstannanes
  作者：Brad M. Savall、Noel A. Powell、William R. Roush

  DOI：10.1021/ol016536m

  日期：2001.9.1

  [GRAPHICS]Propargylic 1,2-anti-diol derivatives 2 and 10 are prepared in high yield and excellent diastereoselectivity by addition of alpha -alkoxypropargyl-stannanes 4a and 4b to aldehydes in the presence of BuSnCl3. We also introduce the use of KF on Celite as a convenient and mild reagent for removal of the organotin waste products of these reactions.