(1S,2S)-1-(benzylamino)-3-[tert-butyl(dimethyl)silyl]oxy-1-phenylpropan-2-ol | 192764-26-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2S)-1-(benzylamino)-3-[tert-butyl(dimethyl)silyl]oxy-1-phenylpropan-2-ol
• CAS: 192764-26-4
• 化学式: C₂₂H₃₃NO₂Si
• 分子量: 371.595
• InChiKey: XCTBKFSOWLMXCE-RTWAWAEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N'-羰基二咪唑 、 (1S,2S)-1-(benzylamino)-3-[tert-butyl(dimethyl)silyl]oxy-1-phenylpropan-2-ol 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 (4S,5S)-3-benzyl-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-phenyl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Stereocontrolled addition of Grignard reagents to α-alkoxy nitrones. Synthesis of syn and anti 3-amino-1,2-diols

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(97)00175-4
• 作为产物：
  描述：

  N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone 在 咪唑 、 copper diacetate 、 氯化二乙基铝 、 对甲苯磺酸 、 溶剂黄146 、 锌 作用下， 以 甲醇 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 (1S,2S)-1-(benzylamino)-3-[tert-butyl(dimethyl)silyl]oxy-1-phenylpropan-2-ol
  参考文献：
  名称：

  Stereocontrolled addition of Grignard reagents to α-alkoxy nitrones. Synthesis of syn and anti 3-amino-1,2-diols

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(97)00175-4

文献信息

• 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
  作者：Pedro Merino、Elena Castillo、Santiago Franco、Francisco L. Merchán、Tomas Tejero

  DOI：10.1016/s0040-4020(98)00741-8

  日期：1998.10

  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.