N-benzyl-N-[(S)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-phenylmethyl]hydroxylamine | 192764-07-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-benzyl-N-[(S)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-phenylmethyl]hydroxylamine
• CAS: 192764-07-1
• 化学式: C₁₉H₂₃NO₃
• 分子量: 313.397
• InChiKey: IHVMYGDTMWXZQI-MSOLQXFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  41.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-benzyl-N-[(S)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-phenylmethyl]hydroxylamine 在 palladium dihydroxide 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 氢气 、 sodium methylate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 37.0h， 生成 甲基(2S,3S)-N-boc-3-苯基异丝氨酸盐酸
  参考文献：
  名称：

  Nucleophilic additions of Grignard reagents to N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone (BIGN). Synthesis of (2S,3R) and (2S,3S)-3-phenylisoserine

  摘要：

  A remarkable Lewis acid tuning has been observed in the nucleophilic addition of Grignard reagent to BIGN, the N-benzyl nitrone derived from 1,2-O-isopropylidene-D-glyceraldehyde. The obtained alpha,beta-dialkoxy hydroxylamines can serve as starting points for the synthesis of both aminodiols and alpha-hydroxy-beta-amino acids. This synthetic approach is illustrated by the synthesis of the antipode of the C-13 side chain of Taxotere as well as its C-3 epimer. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00741-8
• 作为产物：
  描述：

  N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone 、 苯基溴化镁 在 氯化二乙基铝 作用下， 生成 N-benzyl-N-[(S)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-phenylmethyl]hydroxylamine
  参考文献：
  名称：

  Enantiodivergent Approach to d- and l-Secondary N-Hydroxy-α-amino Acids by Using N-Benzyl-2,3-O-isopropylidene-d- glyceraldehyde Nitrone as an Effective N-Hydroxyglycine Cation Equivalent

  摘要：

  DOI：

  10.1021/jo971913n

文献信息

• Stereocontrolled addition of Grignard reagents to α-alkoxy nitrones. Synthesis of syn and anti 3-amino-1,2-diols
  作者：Pedro Merino、Elena Castillo、Francisco L Merchan、Tomas Tejero

  DOI：10.1016/s0957-4166(97)00175-4

  日期：1997.6

  The stereoselective addition of Grignard reagents to alpha-alkoxy nitrones has been achieved with excellent stereocontrol using ZnBr2 and Et2AlCl as precomplexing agents to obtain the corresponding syn- and anti- adducts, respectively. The obtained hydroxylamines have been transformed into valuable 3-amino-1,2-diols. (C) 1997 Elsevier Science Ltd.