methyl (2S,3R,4R)-5-[tert-butyl(diphenyl)silyl]oxy-4-(dibenzylamino)-3-hydroxy-2-phenylmethoxypentanoate | 627859-92-1

• 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: methyl (2S,3R,4R)-5-[tert-butyl(diphenyl)silyl]oxy-4-(dibenzylamino)-3-hydroxy-2-phenylmethoxypentanoate
• CAS: 627859-92-1
• 化学式: C₄₃H₄₉NO₅Si
• 分子量: 687.951
• InChiKey: UAGJFEUJIAOWNG-AXEMHBPCSA-N

物化性质

• 沸点：
  736.3±60.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.75
• 重原子数：
  50
• 可旋转键数：
  18
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  68.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (2S,3R,4R)-5-[tert-butyl(diphenyl)silyl]oxy-4-(dibenzylamino)-3-hydroxy-2-phenylmethoxypentanoate 在 palladium dihydroxide 氢气 、 三甲基铝 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 90.0h， 生成 (3S,4R,5R)-5-(tert-butyldiphenylsilyloxymethyl)-3,4-dihydroxypyrrolidin-2-one
  参考文献：
  名称：

  Stereoselective synthesis of the α-glucosidase inhibitor nectrisine

  摘要：

  The alpha-glucosidase inhibitor nectrisine was synthesised in 12 steps (31%, overall yield) starting from D-serine. The three contiguous stereocentres of this iminosugar were introduced via a highly diastereoselective boron mediated glycolate aldol reaction. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.08.030
• 作为产物：
  描述：

  2-苯基甲氧基乙酸甲酯 、 (2S)-3-(tert-Butyldiphenylsiloxy)-2-(dibenzylamino)propanal 在 三氟甲磺酸二丁硼 、 N,N-二异丙基乙胺 作用下， 以 乙醚 为溶剂， 反应 3.5h， 以75%的产率得到methyl (2S,3R,4R)-5-[tert-butyl(diphenyl)silyl]oxy-4-(dibenzylamino)-3-hydroxy-2-phenylmethoxypentanoate
  参考文献：
  名称：

  Stereoselective synthesis of the α-glucosidase inhibitor nectrisine

  摘要：

  The alpha-glucosidase inhibitor nectrisine was synthesised in 12 steps (31%, overall yield) starting from D-serine. The three contiguous stereocentres of this iminosugar were introduced via a highly diastereoselective boron mediated glycolate aldol reaction. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.08.030

文献信息

• Stereoselective synthesis of the α-glucosidase inhibitor nectrisine
  作者：Alison N. Hulme、Charles H. Montgomery

  DOI：10.1016/j.tetlet.2003.08.030

  日期：2003.10

  The alpha-glucosidase inhibitor nectrisine was synthesised in 12 steps (31%, overall yield) starting from D-serine. The three contiguous stereocentres of this iminosugar were introduced via a highly diastereoselective boron mediated glycolate aldol reaction. (C) 2003 Elsevier Ltd. All rights reserved.