5-t-butyldimethylsilyloxy-1-t-butyldiphenylsilyloxyhexane | 121671-73-6

• 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: 5-t-butyldimethylsilyloxy-1-t-butyldiphenylsilyloxyhexane
• 英文别名: Tert-butyl-[5-[tert-butyl(dimethyl)silyl]oxyhexoxy]-diphenylsilane
• CAS: 121671-73-6
• 化学式: C₂₈H₄₆O₂Si₂
• 分子量: 470.843
• InChiKey: PMWWBHVKPOVJBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.14
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  5-t-butyldimethylsilyloxy-1-t-butyldiphenylsilyloxyhexane 以57%的产率得到
  参考文献：
  名称：

  Feixas Joan, Capdevila Anna, Guerrero Angel, Tetrahedron, 50 (1994) N 28, S 8539-8550

  摘要：

  DOI：
• 作为产物：
  描述：

  1,5-己二醇 在 咪唑 、 sodium hydride 作用下， 生成 5-t-butyldimethylsilyloxy-1-t-butyldiphenylsilyloxyhexane
  参考文献：
  名称：

  Utilization of neutral alumina as a mild reagent for the selective cleavage of primary and secondary silyl ethers

  摘要：

  The selective cleavage of primary and secondary trimethylsilyl (TMS), triisopropylsilyl (TIPS), tert-butyldimethylsilyl (TBDMS) and tert-butyldiphenylsilyl (TBDPS) ethers with neutral alumina under very mild conditions is described. The method involves utilization of the support, previously activated by heating at 80 degrees C/0.1 torr for 16 h and later deactivated with variable amounts of water (1.5-4.5%), in 50:1 ratio with regard to the substrate and in the presence of non-polar solvents, like hexane. The deprotection rate depends on the steric bulkiness of the silicon substituents, following the order TMS > > TBDMS approximate to TIPS > TBDPS, as well as on the type of the attached carbon. The procedure can discriminate between different silyl groups located at equivalent positions of the same molecule affording the corresponding monoprotected alcohols in very good yields.

  DOI：

  10.1016/s0040-4020(01)85572-1

文献信息

• Cleavage of tert-butyldimethylsilyl ethers by chloride ion
  作者：Jaume Farràs、Carme Serra、Jaume Vilarrasa

  DOI：10.1016/s0040-4039(97)10479-8

  日期：1998.1

  A general method for the selective cleavage of tert-butyldimethylsilyl ethers in the presence of tert-butyldiphenylsilyl ones has been established using a combination of H2O and a concentrated solution of LiCl in DMF at 90 °C. Since no acids, bases, reducing or oxidizing agents are used, the method seems to be very appropiate for the deprotection of TBDMS ethers in the presence of other sensitive functional

  对的选择性裂解的一般方法叔丁基二醇醚的存在下叔使用H的组合已经建立-butyldiphenylsilyl者2 O和氯化锂的DMF在90℃下的浓缩溶液。由于不使用酸，碱，还原剂或氧化剂，因此该方法似乎非常适合在存在其他敏感官能团的情况下对TBDMS醚进行脱保护。
• Higashibayashi; Shinko; Ishizu, Synlett, 2000, # 9, p. 1306 - 1308
  作者：Higashibayashi、Shinko、Ishizu、Hashimoto、Shirahama、Nakata

  DOI：——

  日期：——
• Selective de-protection of silyl ethers
  作者：Chandra Prakash、Samir Saleh、Ian A. Blair

  DOI：10.1016/s0040-4039(01)80311-7

  日期：——
• Feixas Joan, Capdevila Anna, Guerrero Angel, Tetrahedron, 50 (1994) N 28, S 8539-8550
  作者：Feixas Joan, Capdevila Anna, Guerrero Angel

  DOI：——

  日期：——
• PRAKASH, CHANDRA;SALEH, SAMIR;BLAIR, IAN A., TETRAHEDRON LETT., 30,(1989) N 1, C. 19-22
  作者：PRAKASH, CHANDRA、SALEH, SAMIR、BLAIR, IAN A.

  DOI：——

  日期：——