tert-butyl N-[(2R,3S)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoyl]-N-phenylcarbamate | 889472-39-3

• 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: tert-butyl N-[(2R,3S)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoyl]-N-phenylcarbamate
• CAS: 889472-39-3
• 化学式: C₂₂H₃₄N₂O₅
• 分子量: 406.522
• InChiKey: FGBTTWSRLOOBBG-DOTOQJQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(2R,3S)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoyl]-N-phenylcarbamate 在 lithium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 N-叔丁氧羰基-D-别异亮氨酸
  参考文献：
  名称：

  Asymmetric, anti-Selective Scandium-Catalyzed Sakurai Additions to Glyoxyamide. Applications to the Syntheses of N-Boc d-Alloisoleucine and d-Isoleucine

  摘要：

  An enantio- and diastereoselective Sakurai-Hosomi reaction, catalyzed by chiral scandium pyridyl-bis(oxazoline) (pybox) complexes, has been developed. Both alkyl- and aryl-substituted allylsilanes are effective coupling partners with N-phenylglyoxamide. Applications of this reaction to the asymmetric syntheses of N-BOC D-alloisoleucine and D-isoleucine are described.

  DOI：

  10.1021/ol0604771
• 作为产物：
  描述：

  N-phenyl-3-methyl-2-butenamide 在 palladium on activated charcoal 4-二甲氨基吡啶 、 sodium azide 、 (S,S)-bis(oxazolinyl)pyridine ligand 、 4 A molecular sieve 、 氢气 、 氧气 、 臭氧 、 三乙胺 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， -78.0~70.0 ℃ 、101.33 kPa 条件下， 生成 tert-butyl N-[(2R,3S)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoyl]-N-phenylcarbamate
  参考文献：
  名称：

  Asymmetric, anti-Selective Scandium-Catalyzed Sakurai Additions to Glyoxyamide. Applications to the Syntheses of N-Boc d-Alloisoleucine and d-Isoleucine

  摘要：

  An enantio- and diastereoselective Sakurai-Hosomi reaction, catalyzed by chiral scandium pyridyl-bis(oxazoline) (pybox) complexes, has been developed. Both alkyl- and aryl-substituted allylsilanes are effective coupling partners with N-phenylglyoxamide. Applications of this reaction to the asymmetric syntheses of N-BOC D-alloisoleucine and D-isoleucine are described.

  DOI：

  10.1021/ol0604771

文献信息

• Asymmetric, <i>anti</i>-Selective Scandium-Catalyzed Sakurai Additions to Glyoxyamide. Applications to the Syntheses of <i>N</i>-Boc <scp>d</scp>-Alloisoleucine and <scp>d</scp>-Isoleucine
  作者：David A. Evans、Yimon Aye、Jimmy Wu

  DOI：10.1021/ol0604771

  日期：2006.5.1

  An enantio- and diastereoselective Sakurai-Hosomi reaction, catalyzed by chiral scandium pyridyl-bis(oxazoline) (pybox) complexes, has been developed. Both alkyl- and aryl-substituted allylsilanes are effective coupling partners with N-phenylglyoxamide. Applications of this reaction to the asymmetric syntheses of N-BOC D-alloisoleucine and D-isoleucine are described.