tert-butyl N-[(S)-[diethoxy(oxido)phosphaniumyl]-[(1R,2S)-2-hydroxycyclopentyl]methyl]carbamate | 1093380-72-3

• 英文名称: tert-butyl N-[(S)-[diethoxy(oxido)phosphaniumyl]-[(1R,2S)-2-hydroxycyclopentyl]methyl]carbamate
• CAS: 1093380-72-3
• 化学式: C₁₅H₃₀NO₆P
• 分子量: 351.38
• InChiKey: QAXOKBJATNAQLL-AGIUHOORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  100
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  diethyl (3S,3aR,6aS)-hexahydro-2-[(S)-1-phenylethyl]-2H-cyclopenta[d]isoxazol-3-yl-3-phosphonate 、 二碳酸二叔丁酯 在 Pd(OH)2/C 、 10% Pd/C 、 氢气 作用下， 以 乙醇 为溶剂， 反应 15.0h， 以10%的产率得到tert-butyl N-[(S)-[diethoxy(oxido)phosphaniumyl]-[(1R,2S)-2-hydroxycyclopentyl]methyl]carbamate
  参考文献：
  名称：

  Stereochemistry of cycloaddition of (S)-N-(1-phenylethyl)-C-phosphorylated nitrone with cyclopentene and 2,3-dihydrofuran

  摘要：

  Cycloaddition of(S)-N-(1-phenylethyl)-C-(diethoxyphosphoryl)nitrone to cyclopentene gave a mixture of diethyl (3S,3aR,6aS)- and (3R,3aS,6aR)-hexahydro-2-[(S)-1-phenylethyl-2H-cyclopenta[d]isoxazol-3-yl-3-phosphonates with moderate (68:32) diastereoselectivity, while the reaction with 2,3-dihydrofuran led regiospecifically to the formation of an easily separable mixture of diethyl (3S,3aR,6aR)- and (3R,3aS,6aS)-hexahydro-2-[(S)-1-phenylethyl]furo[3,2-d]isoxazol-3-yl-3-phosphonates in a 65:35 ratio. Absolute configurations of cycloadducts Were established based on conformational analyses employing H-1 and C-13 NMR data and confirmed by 2D NOE experiments. Diastereoisomeric diethyl (3S,3aR,6aS)and (3R,3aS,6aR)-hexahydro-2-[(S)-1-phenylethyl-2H-cyclopenata[d]isoxazol-3-yl-3-phosphonates were transformed into both enantiomers of tert-butyl (2S,3S,3aR,6aS)- and (2R,3R,3aS,6aR)-2-ethoxy-2-oxo-cyclopenta[d](1,2-oxaphospholan-3-yl)carbamates in good yields. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.09.027