(2R,3S)-N-benzyloxycarbonyl-3-phenylserine methyl ester | 207396-23-4

• 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: (2R,3S)-N-benzyloxycarbonyl-3-phenylserine methyl ester
• 英文别名: threo-3-Phenyl-N-benzyloxycarbonyl-serin-methylester；methyl (2R,3S)-3-hydroxy-3-phenyl-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 207396-23-4
• 化学式: C₁₈H₁₉NO₅
• 分子量: 329.353
• InChiKey: VKODCPRHLXHHEG-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-(苄羰氧基)羟基胺 在 四氧化锇 、 氢化奎宁 1,4-(2,3-二氮杂萘)二醚 、 三乙胺 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 0.17h， 生成 (2R,3S)-N-benzyloxycarbonyl-3-phenylserine methyl ester
  参考文献：
  名称：

  Alkyl 4-Chlorobenzoyloxycarbamates as Highly Effective Nitrogen Source Reagents for the Base-Free, Intermolecular Aminohydroxylation Reaction

  摘要：

  Ethyl- (7), benzyl- (8), tert-butyl- (9), and fluorenylmethyl-4-chlorobenzoyloxycarbamates (10) have been prepared as storable and easy-to-prepare nitrogen sources for use in the intermolecular Sharpless aminohydroxylation reaction and its asymmetric variant. These reagents were found to be effective under base-free reaction conditions. The scope and limitations of these methods have been explored using a variety of alkenes, among which, trans-cinnamates, in particular, proved to be good substrates.

  DOI：

  10.1021/jo1018816

文献信息

• Reversal of regioselection in the asymmetric aminohydroxylation of cinnamates
  作者：Beata Tao、Gunther Schlingloff、K.Barry Sharpless

  DOI：10.1016/s0040-4039(98)00350-5

  日期：1998.4

  Use of cinchona ligands with an anthraquinone (AQN) core, in place of the usual phthalazine (PHAL) core, in the asymmetric aminohydroxylation of cinnamates causes dramatic reversal of the regioselection, so that phenyl serines are obtained in high enantiomeric excess. Hence, the regioselectivity outcome (i.e. isoserine vs. serine) is controlled by the ligand and not the substrate. (C) 1998 Elsevier Science Ltd. All rights reserved.