1-(tetrahydrofuran-2-yl)-1-trimethylsilanylethanol | 1221235-10-4

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 1-(tetrahydrofuran-2-yl)-1-trimethylsilanylethanol
• CAS: 1221235-10-4
• 化学式: C₉H₂₀O₂Si
• 分子量: 188.342
• InChiKey: CQXHLPWJXPUCBG-UHFFFAOYSA-N

反应信息

• 作为产物：
  描述：

  3-(3-methyl-3-trimethylsilanyl-oxiranyl)-propan-1-ol 在 caesium carbonate 作用下， 以 甲醇 为溶剂， 反应 20.0h， 生成 1-(tetrahydrofuran-2-yl)-1-trimethylsilanylethanol 、 (2R,3R)-2-methyl-2-trimethylsilanyl-tetrahydro-pyran-3-ol
  参考文献：
  名称：

  Ladder Polyether Synthesis via Epoxide-Opening Cascades Directed by a Disappearing Trimethylsilyl Group

  摘要：

  Epoxide-opening cascades offer the potential to construct complex polyether natural products expeditiously and in a manner that emulates the biogenesis proposed for these compounds. Herein we provide a full account of our development of a strategy that addresses several important challenges of such cascades. The centerpiece of the method is a trimethylsilyl (SiMe3) group that serves several purposes and leaves no trace of itself by the time the cascade has come to an end. The main function of the SiMe3 group is to dictate the regioselectivity of epoxide opening. This strategy is the only general method of effecting endo-selective cascades under basic conditions.

  DOI：

  10.1021/jo1002455

文献信息

• Gold‐catalyzed <i>endo</i>‐selective Ring‐opening of Epoxides and its Application in Construction of Poly‐ethers
  作者：Kehuan Wu、Kaiwen Kang、Dan Liu、Chiyue Zhang、Xinyu Wang、Miaocheng Zhang、Qi Li

  DOI：10.1002/chem.202400234

  日期：2024.4.11

  Tetrahydropyran and tetrahydropyran‐fused poly‐ethers scaffolds are found in many classes of natural products and medicinally relevant small molecules. Here we describe a catalytic system for 6‐endo selective ring‐opening of epoxides by Au(I) or Au(III) catalyst that provides rapid access to various tetrahydropyran‐derived motifs. It also could efficiently construct the subunits of marine ladder‐like poly‐ethers through emulating the Nakanishi's hypothesis on the biosynthesis of these toxins. The synthetic utility of this method is also demonstrated in the preparation of the tricyclic core of tetrahydropyran‐containing macrolide natural products lituarines A−C.

  摘要四氢吡喃和四氢吡喃融合聚醚支架存在于许多天然产品和药用小分子中。在此，我们介绍了一种利用金（I）或金（III）催化剂进行环氧化物 6 内向选择性开环的催化系统，该系统可快速获得各种四氢吡喃衍生基团。它还可以通过模仿中西（Nakanishi）关于这些毒素生物合成的假说，有效地构建海洋梯状聚醚的亚基。在制备含四氢吡喃的大环内酯天然产物 lituarines A-C 的三环核心时，也证明了该方法的合成实用性。