tert-butyl N-[(2R,4S)-4-[tert-butyl(dimethyl)silyl]oxy-1-hydroxy-5-[(2-methylpropan-2-yl)oxycarbonylamino]pentan-2-yl]carbamate | 1022533-55-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: tert-butyl N-[(2R,4S)-4-[tert-butyl(dimethyl)silyl]oxy-1-hydroxy-5-[(2-methylpropan-2-yl)oxycarbonylamino]pentan-2-yl]carbamate
• CAS: 1022533-55-6
• 化学式: C₂₁H₄₄N₂O₆Si
• 分子量: 448.676
• InChiKey: BTRHZGDSEPDDRG-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  30
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  106
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(2R,4S)-4-[tert-butyl(dimethyl)silyl]oxy-1-hydroxy-5-[(2-methylpropan-2-yl)oxycarbonylamino]pentan-2-yl]carbamate 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 sodium chlorite 作用下， 以 乙腈 为溶剂， 以82%的产率得到(2R,4S)-4-[tert-butyl(dimethyl)silyl]oxy-2,5-bis[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid
  参考文献：
  名称：

  A concise synthesis of protected (2S,4R)-4-hydroxyornithine

  摘要：

  A short synthesis of the nonproteinogenic amino acid, (2S,4R)-4-hydroxyornithine is described. Starting from racemic benzyl glycidol, the scaffold of the target compound was constructed in high enantio- and diastereoselectivity using Jacobsen's hydrolytic kinetic resolution (HKR) and regioselective opening of an epoxide as key steps. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.03.076
• 作为产物：
  描述：

  tert-butyl-[(2S,4R)-1,4-diazido-5-phenylmethoxypentan-2-yl]oxy-dimethylsilane 、 二碳酸二叔丁酯 在 palladium dihydroxide 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 12.0h， 以86%的产率得到tert-butyl N-[(2R,4S)-4-[tert-butyl(dimethyl)silyl]oxy-1-hydroxy-5-[(2-methylpropan-2-yl)oxycarbonylamino]pentan-2-yl]carbamate
  参考文献：
  名称：

  A concise synthesis of protected (2S,4R)-4-hydroxyornithine

  摘要：

  A short synthesis of the nonproteinogenic amino acid, (2S,4R)-4-hydroxyornithine is described. Starting from racemic benzyl glycidol, the scaffold of the target compound was constructed in high enantio- and diastereoselectivity using Jacobsen's hydrolytic kinetic resolution (HKR) and regioselective opening of an epoxide as key steps. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.03.076

文献信息

• A concise synthesis of protected (2S,4R)-4-hydroxyornithine
  作者：Satyendra Kumar Pandey、Menaka Pandey、Pradeep Kumar

  DOI：10.1016/j.tetlet.2008.03.076

  日期：2008.5

  A short synthesis of the nonproteinogenic amino acid, (2S,4R)-4-hydroxyornithine is described. Starting from racemic benzyl glycidol, the scaffold of the target compound was constructed in high enantio- and diastereoselectivity using Jacobsen's hydrolytic kinetic resolution (HKR) and regioselective opening of an epoxide as key steps. (c) 2008 Elsevier Ltd. All rights reserved.