3-O-tert-butyl 5-O-methyl (4S,5R)-4-(4-fluorophenyl)-2,2-dimethyl-1,3-oxazolidine-3,5-dicarboxylate | 154306-86-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-O-tert-butyl 5-O-methyl (4S,5R)-4-(4-fluorophenyl)-2,2-dimethyl-1,3-oxazolidine-3,5-dicarboxylate
• CAS: 154306-86-2
• 化学式: C₁₈H₂₄FNO₅
• 分子量: 353.391
• InChiKey: VXHUAYCJRMWBBT-UONOGXRCSA-N

物化性质

• 沸点：
  413.0±45.0 °C(predicted)
• 密度：
  1.168±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.41
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  65.07
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-O-tert-butyl 5-O-methyl (4S,5R)-4-(4-fluorophenyl)-2,2-dimethyl-1,3-oxazolidine-3,5-dicarboxylate 在 4-二甲氨基吡啶 、 甲酸 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 为溶剂， 反应 5.0h， 生成 N-de-tert-butoxycarbonyl-N-[2-(1,1,1-trifluoro-2-methyl)propyloxycarbonyl]-7,10-di-(2,2,2-trichloroethyloxycarbonyl)-3-dephenyl-3'-(4-fluorophenyl)docetaxel
  参考文献：
  名称：

  Synthesis, cytotoxicity, metabolic stability and pharmacokinetic evaluation of fluorinated docetaxel analogs

  摘要：

  Three novel fluorinated docetaxel analogs, along with six previous reported, were evaluated for their cytotoxicity against five tumor cell lines. The results indicated that these analogs maintained similar/ more potent activity than docetaxel against these tumor cell lines. They were also evaluated for their metabolic stability and pharmacokinetics, which demonstrated that these analogs showed better profiles of metabolic stability and pharmacokinetics than that of docetaxel. Crown Copyright (C) 2011 Published by Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.02.027
• 作为产物：
  描述：

  methyl (2R,3S)-3-amino-2-hydroxy-3-(4-fluoro-phenyl)propionate 在 4-甲基苯磺酸吡啶 、 sodium carbonate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 72.0h， 生成 3-O-tert-butyl 5-O-methyl (4S,5R)-4-(4-fluorophenyl)-2,2-dimethyl-1,3-oxazolidine-3,5-dicarboxylate
  参考文献：
  名称：

  A practical access to chiral phenylisoserinates, preparation of Taxotere® analogs

  摘要：

  A practical diastereoselective synthesis of phenylisoserine methyl esters 8a-c is described using alpha-methyl-benzylamine as the chiral template of a Staudinger reaction. Optically pure diastereoisomers 6a-c were easily recovered by crystallization. After opening of these intermediate azetidinones by hydrochloric acid and methanol, regioselective cleavage of the chiral auxiliary was achieved by hydrogenation over palladium. Phenylisoserinates 8b,c were used to prepare analogs of Taxotere(R).

  DOI：

  10.1016/s0040-4039(00)61724-0

文献信息

• Synthesis of Taxoids I. Regioselective Lewis Acid-mediated Ring-opening of Aryl Orthoacetates
  作者：Tomiki Hashiyama、Naoyuki Harada、Kunihiko Ozaki、Tetsuo Yamaguchi、Akira Ando、Kenji Tsujihara

  DOI：10.3987/com-96-s20

  日期：——