((2R,3R,4S,5R,6S)-6-phenoxy-3,4,5-tris((trimethylsilyl)oxy)tetrahydro-2H-pyran-2-yl)methanol | 1443504-00-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((2R,3R,4S,5R,6S)-6-phenoxy-3,4,5-tris((trimethylsilyl)oxy)tetrahydro-2H-pyran-2-yl)methanol
• CAS: 1443504-00-4
• 化学式: C₂₁H₄₀O₆Si₃
• 分子量: 472.801
• InChiKey: JRYGXFGAAOSOGS-YMQHIKHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.44
• 重原子数：
  30.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  (((2S,3R,4S,5R,6R)-2-phenoxy-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl)tris(oxy))tris(trimethylsilane) 在 ammonium acetate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 9.0h， 以85%的产率得到((2R,3R,4S,5R,6S)-6-phenoxy-3,4,5-tris((trimethylsilyl)oxy)tetrahydro-2H-pyran-2-yl)methanol
  参考文献：
  名称：

  Regioselective 6-detrimethylsilylation of per-O-TMS-protected carbohydrates in the presence of ammonium acetate

  摘要：

  A convenient methodology has been developed for the regioselective removal of primary trimethylsilyl group (TMS) of various per-O-TMS-protected carbohydrates by inexpensive ammonium acetate. After acetylation and trichloroacetimidation of 6-hydroxyl sugar 1b, other TMS groups of 1d and 1c were inert to ammonium acetate in the same conditions, and this approach was also successfully applied in TMS-protected sphingosine. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.039