(E)-3-[(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-prop-2-en-1-ol | 524706-28-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (E)-3-[(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-prop-2-en-1-ol
• 英文别名: (E)-3-[(2R,3S)-3-[tert-butyl(dimethyl)silyl]oxyoxan-2-yl]prop-2-en-1-ol
• CAS: 524706-28-3
• 化学式: C₁₄H₂₈O₃Si
• 分子量: 272.46
• InChiKey: SJRUNXCIPCBXDS-DZTBXEGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-[(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-prop-2-en-1-ol 在 platinum(IV) oxide 氢气 作用下， 以 甲醇 为溶剂， 以100%的产率得到3-[(2R,3S)-3-(tert-butyldimethylsilanyloxy)tetrahydropyran-2-yl]propan-1-ol
  参考文献：
  名称：

  Stereoselective Synthesis of Cyclic Ethers by Intramolecular Trapping of Dicobalt Hexacarbonyl-Stabilized Propargylic Cations

  摘要：

  The intramolecular attack of a hydroxy group on an exo-biscobalthexacarbonyl propargylic cation provides cyclic ethers with six- to nine-membered rings. The scope and limitations of the methodology are described. The reaction is stereoselective when additional stereocenters are present, providing iterative methodology to access ladder-like cyclic ethers.

  DOI：

  10.1021/jo0340556
• 作为产物：
  描述：

  (2'R,3'S)-<3'-(tert-butyldimethylsilyloxy)tetrahydropyran-2'-yl>methanol 在 lithium aluminium tetrahydride 、 三氯化铝 、 草酰氯 、 sodium hydride 、 二甲基亚砜 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 苯 为溶剂， 生成 (E)-3-[(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-prop-2-en-1-ol
  参考文献：
  名称：

  The tert-butyl dimethyl silyl group as an enhancer of drug cytotoxicity against human tumor cells

  摘要：

  In this study, we synthesized a series of enantiomerically pure (2R,3S)-disubstituted tetrahydropyranes with diverse functional groups using known methodologies. In addition to the tert-butyl dimethyl silyl group, other common protecting groups for hydroxyl groups such as allyl, acetate, and benzoate were used to obtain appropriate derivatives. Pure compounds were evaluated in vitro against HL60 human leukemia cells and MCF7 human breast cancer cells. From the growth inhibition data a structure-activity relationship was obtained. Overall the results point to the relevant role of the tert-butyl dimethyl silyl group in the modulation of cytotoxic activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.126

文献信息

• The tert-butyl dimethyl silyl group as an enhancer of drug cytotoxicity against human tumor cells
  作者：Osvaldo J. Donadel、Tomás Martín、Víctor S. Martín、Jesús Villar、José M. Padrón

  DOI：10.1016/j.bmcl.2005.05.126

  日期：2005.8

  In this study, we synthesized a series of enantiomerically pure (2R,3S)-disubstituted tetrahydropyranes with diverse functional groups using known methodologies. In addition to the tert-butyl dimethyl silyl group, other common protecting groups for hydroxyl groups such as allyl, acetate, and benzoate were used to obtain appropriate derivatives. Pure compounds were evaluated in vitro against HL60 human leukemia cells and MCF7 human breast cancer cells. From the growth inhibition data a structure-activity relationship was obtained. Overall the results point to the relevant role of the tert-butyl dimethyl silyl group in the modulation of cytotoxic activity. (c) 2005 Elsevier Ltd. All rights reserved.
• Stereoselective Synthesis of Cyclic Ethers by Intramolecular Trapping of Dicobalt Hexacarbonyl-Stabilized Propargylic Cations
  作者：Juan M. Betancort、Tomás Martín、José M. Palazón、Víctor S. Martín

  DOI：10.1021/jo0340556

  日期：2003.4.1

  The intramolecular attack of a hydroxy group on an exo-biscobalthexacarbonyl propargylic cation provides cyclic ethers with six- to nine-membered rings. The scope and limitations of the methodology are described. The reaction is stereoselective when additional stereocenters are present, providing iterative methodology to access ladder-like cyclic ethers.