2-((2R,5S)-5-((S)-2-(tert-butyldimethylsilyloxy)-1-hydroxyethyl)-5-methyltetrahydrofuran-2-yl)propan-2-ol | 1174400-50-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: 2-((2R,5S)-5-((S)-2-(tert-butyldimethylsilyloxy)-1-hydroxyethyl)-5-methyltetrahydrofuran-2-yl)propan-2-ol
• 英文别名: 2-[(2R,5S)-5-[(1S)-2-[tert-butyl(dimethyl)silyl]oxy-1-hydroxyethyl]-5-methyloxolan-2-yl]propan-2-ol
• CAS: 1174400-50-0
• 化学式: C₁₆H₃₄O₄Si
• 分子量: 318.529
• InChiKey: NETDSHMNVCGUSL-ZENOOKHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.08
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-((2R,5S)-5-((S)-2-(tert-butyldimethylsilyloxy)-1-hydroxyethyl)-5-methyltetrahydrofuran-2-yl)propan-2-ol 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  A Lewis Acid Promoted Oxidative Cyclization

  摘要：

  Replacing trifluoroacetic acid with it catalytic amount of Lewis acid in the osmium mediated oxidative cyclization results in higher yielding reactions that can proceed nearly an order of magnitude faster. The osmium loading can also be reduced to as little its 0.2 mol %. Furthermore, these mildly acidic conditions are capable of tolerating a wide range of acid sensitive protecting groups that are incompatible with previous cyclization conditions.

  DOI：

  10.1021/jo901243y
• 作为产物：
  描述：

  (R,E)-8-(tert-butyldimethylsilyloxy)-2,6-dimethyloct-6-ene-2,3-diol 在 吡啶-N-氧化物 、 potassium osmate(VI) dihydrate 、 copper(II) bis(trifluoromethanesulfonate) 、 柠檬酸 、 sodium sulfite 作用下， 以 乙腈 为溶剂， 反应 36.5h， 以67%的产率得到2-((2R,5S)-5-((S)-2-(tert-butyldimethylsilyloxy)-1-hydroxyethyl)-5-methyltetrahydrofuran-2-yl)propan-2-ol
  参考文献：
  名称：

  A Lewis Acid Promoted Oxidative Cyclization

  摘要：

  Replacing trifluoroacetic acid with it catalytic amount of Lewis acid in the osmium mediated oxidative cyclization results in higher yielding reactions that can proceed nearly an order of magnitude faster. The osmium loading can also be reduced to as little its 0.2 mol %. Furthermore, these mildly acidic conditions are capable of tolerating a wide range of acid sensitive protecting groups that are incompatible with previous cyclization conditions.

  DOI：

  10.1021/jo901243y

文献信息

• A Highly Efficient Procedure for Ruthenium Tetroxide Catalyzed Oxidative Cyclizations of 1,5-Dienes
  作者：Stefanie Roth、Sabrina Göhler、Huan Cheng、Christian B. W. Stark

  DOI：10.1002/ejoc.200500052

  日期：2005.10

  for the oxidative cyclization of 1,5-dienes, which generally allows for high yields and selectivities. A solid-supported terminal oxidant and a finely tuned solvent mixture have both been identified as critical factors for this high efficiency. As little as 0.2 mol-% ruthenium(III) chloride as a pre-catalyst for the ruthenium tetroxide generated in situ is required to accomplish oxidative cyclization

  我们报告了一种用于 1,5-二烯氧化环化的高效程序，该程序通常允许高产率和选择性。固体负载的末端氧化剂和微调的溶剂混合物都被认为是实现这种高效率的关键因素。需要低至 0.2 mol% 的氯化钌 (III) 作为原位生成的四氧化钌的预催化剂来完成氧化环化。这种极低的催化剂负载量、高非对映选择性、温和的反应条件和简单的后处理程序是该工艺的关键特征。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)