1-(tert-butyldimethylsilyloxy)-6-(triisopropylsilyloxy)hexane

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 1-(tert-butyldimethylsilyloxy)-6-(triisopropylsilyloxy)hexane
• 英文别名: Tert-butyl-dimethyl-[6-tri(propan-2-yl)silyloxyhexoxy]silane；tert-butyl-dimethyl-[6-tri(propan-2-yl)silyloxyhexoxy]silane
• 化学式: C₂₁H₄₈O₂Si₂
• 分子量: 388.782
• InChiKey: NQOTVARIOFIHMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.76
• 重原子数：
  25
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(tert-butyldimethylsilyloxy)-6-(triisopropylsilyloxy)hexane 在 1-氯乙基氯甲酸酯 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以86%的产率得到6-((triisopropylsilyl)oxy)hexan-1-ol
  参考文献：
  名称：

  Efficient chemoselective deprotection of silyl ethers using catalytic 1-chloroethyl chloroformate in methanol

  摘要：

  Fast and chemoselective desilylation of silyl-protected alcohols was achieved using a catalytic amount of 1-chloroethyl chloroformate in methanol. With a minimal amount of 1-chloroethyl chloroformate as the source for anhydrous HCl, extremely efficient cleavage of silyl ethers of primary and secondary alcohols was accomplished, and chemoselective deprotection of one silyl ether in the presence of another silyl or other acid-labile group was possible through controlling the amount of the chloroformate and reaction time. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.10.043

文献信息

• Mild and Selective Deprotection of tert-Butyl(dimethyl)silyl Ethers with Catalytic­ Amounts of Sodium Tetrachloroaurate(III) Dihydrate
  作者：Qi Zhang、Yonghai Chai、Xiuqin Kang、Lei Long、Lijuan Zhu

  DOI：10.1055/s-0034-1379032

  日期：——

  permits selective deprotection of aliphatic TBS ethers in good to excellent yields in the presence of aromatic TBS ethers, aliphatic triisopropylsilyl ethers, aliphatic tert-butyl(diphenyl)silyl ethers, or sterically hindered aliphatic TBS ethers. Additionally, TBS ethers can also be transformed into 4-methoxybenzyl ethers or methyl ethers in one pot by using larger quantities of the catalyst and a higher

  摘要 描述了一种简单温和的方法，该方法用催化量的二水合四氯金酸钠（III）二水合物除去叔丁基（二甲基）甲硅烷基（TBS）保护基。该方法允许在芳族TBS醚，脂族三异丙基甲硅烷基醚，脂族叔丁基（二苯基）甲硅烷基醚或空间受阻的脂族TBS醚的存在下，以良好的产率至优异的产率对脂族TBS醚进行选择性脱保护。另外，通过使用较大量的催化剂和较高的反应温度，也可以在一锅中将TBS醚转化为4-甲氧基苄基醚或甲基醚。 描述了一种简单温和的方法，该方法用催化量的二水合四氯金酸钠（III）二水合物除去叔丁基（二甲基）甲硅烷基（TBS）保护基。该方法允许在芳族TBS醚，脂族三异丙基甲硅烷基醚，脂族叔丁基（二苯基）甲硅烷基醚或空间受阻的脂族TBS醚的存在下，以良好的产率至优异的产率对脂族TBS醚进行选择性脱保护。另外，通过使用较大量的催化剂和较高的反应温度，也可以在一锅中将TBS醚转化为4-甲氧基苄基醚或甲基醚。
• ZrCl4 as a mild and efficient catalyst for the one-pot conversion of TBS and THP ethers to acetates
  作者：Ch.Sanjeeva Reddy、G Smitha、S Chandrasekhar

  DOI：10.1016/s0040-4039(03)01078-5

  日期：2003.6

  A mild, efficient and chemoselective method has been developed for the direct transformation of tert-butyldimethylsilyl and tetrahydropyranyl protected alcohols into the corresponding acetates with acetic anhydride and zirconium(IV) chloride as the catalyst in acetonitrile, in a one-pot reaction with high yields and short reaction times. This method has been applied to a variety of substrates. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Efficient chemoselective deprotection of silyl ethers using catalytic 1-chloroethyl chloroformate in methanol
  作者：Chang-Eun Yeom、Young Jong Kim、So Young Lee、Yong Je Shin、B. Moon Kim

  DOI：10.1016/j.tet.2005.10.043

  日期：2005.12

  Fast and chemoselective desilylation of silyl-protected alcohols was achieved using a catalytic amount of 1-chloroethyl chloroformate in methanol. With a minimal amount of 1-chloroethyl chloroformate as the source for anhydrous HCl, extremely efficient cleavage of silyl ethers of primary and secondary alcohols was accomplished, and chemoselective deprotection of one silyl ether in the presence of another silyl or other acid-labile group was possible through controlling the amount of the chloroformate and reaction time. (c) 2005 Elsevier Ltd. All rights reserved.