(2R,3R)-5-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-pentane-1,2-diol | 142387-14-2

• 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: (2R,3R)-5-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-pentane-1,2-diol
• CAS: 142387-14-2
• 化学式: C₂₂H₃₂O₃Si
• 分子量: 372.58
• InChiKey: BBOWRCWHCMJZSX-NQIIRXRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.94
• 重原子数：
  26.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  49.69
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2R,3R)-5-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-pentane-1,2-diol 在 sodium periodate 作用下， 以 叔丁醇 为溶剂， 生成 (R)-4-((tert-butyldiphenylsilyl)oxy)-2-methylbutanal
  参考文献：
  名称：

  Towards the Synthesis of Calyculin: A Synthetic Intermediate Corresponding to the C(26)-C(37) Fragment

  摘要：

  The synthetic intermediate 2 corresponding to the C(26)-C(37) fragment of calyculin A (1) has been synthesized. Key transformations include the efficient one-pot construction of the oxazole system embedded in 1 without epimerization-alpha [C(30)] to the ring, and the in situ formation of the dimethylamine by opening an N-methyllactam with Meerwein's reagent and trapping the resultant methylamine with formaldehyde.

  DOI：

  10.1016/0040-4039(92)88107-g
• 作为产物：
  描述：

  三甲基铝 、 ((2S,3S)-3-(2-(tert-butyldiphenylsilyloxy)ethyl)oxiran-2-yl)methanol 以 正戊烷 为溶剂， 以91%的产率得到(2R,3R)-5-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-pentane-1,2-diol
  参考文献：
  名称：

  Towards the Synthesis of Calyculin: A Synthetic Intermediate Corresponding to the C(26)-C(37) Fragment

  摘要：

  The synthetic intermediate 2 corresponding to the C(26)-C(37) fragment of calyculin A (1) has been synthesized. Key transformations include the efficient one-pot construction of the oxazole system embedded in 1 without epimerization-alpha [C(30)] to the ring, and the in situ formation of the dimethylamine by opening an N-methyllactam with Meerwein's reagent and trapping the resultant methylamine with formaldehyde.

  DOI：

  10.1016/0040-4039(92)88107-g

文献信息

• Total synthesis of (6Z,9S)-3,4-trans-9-hydroxy-3-methyldodec-cis-6-en-4-olide and (6Z)-3,4-trans-9-oxo-3-methyldodec-cis-6-en-4-olide γ-butyrolactones
  作者：Galla Raju、Rajesh Nomula、Kallaganti V.S. Ramakrishna、Palakodety Radha Krishna

  DOI：10.1016/j.tetlet.2014.10.066

  日期：2014.12

  The first total synthesis of (6Z,9S)-3,4-trans-9-hydroxy-3-methyldodec-cis-6-en-4-olide and (6Z)-3,4-trans-9-oxo-3-methyldodec-cis-6-en-4-olide was achieved in a convergent pathway. The salient features of our synthesis include Ohira-Bestmann reaction, regioselective alkyne addition to terminal epoxide, TEMPO/BAIB mediated oxidative lactonization, and partial hydrogenation. (C) 2014 Elsevier Ltd. All rights reserved.