(4R,5R)-tert-butyl 4-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-5-(2-phenylethynyl)oxazolidine-3-carboxylate | 906528-93-6

• 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: (4R,5R)-tert-butyl 4-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-5-(2-phenylethynyl)oxazolidine-3-carboxylate
• CAS: 906528-93-6
• 化学式: C₃₅H₄₃NO₄Si
• 分子量: 569.816
• InChiKey: PNMVRYSDZTVYRH-FIRIVFDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.36
• 重原子数：
  41.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  48.0
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (4R,5R)-tert-butyl 4-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-5-(2-phenylethynyl)oxazolidine-3-carboxylate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.25h， 以91%的产率得到(4R,5R)-tert-butyl 4-(hydroxymethyl)-2,2-dimethyl-5-(2-phenylethynyl)oxazolidine-3-carboxylate
  参考文献：
  名称：

  Synthesis and biological evaluation of novel PDMP analogues

  摘要：

  A new series of hybrid PDMP analogues, based both on PDMP and styryl analogues of natural ceramide, has been synthesized from D-serine. The synthetic route was developed such that future introduction of different aryl groups is straightforward. Biological evaluation, both in vitro on rat liver Golgi fractions as well as in HEK-293 and COS-7 cells, revealed two lead compounds with comparable inhibitory potency as PDMP, which could be elaborated to more potent inhibitors. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.03.048
• 作为产物：
  描述：

  lithium phenylacetylide 在 咪唑 、 4-二甲氨基吡啶 、 对甲苯磺酸 、 zinc dibromide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 58.0h， 生成 (4R,5R)-tert-butyl 4-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-5-(2-phenylethynyl)oxazolidine-3-carboxylate
  参考文献：
  名称：

  Synthesis and biological evaluation of novel PDMP analogues

  摘要：

  A new series of hybrid PDMP analogues, based both on PDMP and styryl analogues of natural ceramide, has been synthesized from D-serine. The synthetic route was developed such that future introduction of different aryl groups is straightforward. Biological evaluation, both in vitro on rat liver Golgi fractions as well as in HEK-293 and COS-7 cells, revealed two lead compounds with comparable inhibitory potency as PDMP, which could be elaborated to more potent inhibitors. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.03.048