(2S)-2-(t-butoxycarbonylamino)-1-(t-butyldimethylsilanyloxy)heptadecan-3-one | 693288-24-3

• 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: (2S)-2-(t-butoxycarbonylamino)-1-(t-butyldimethylsilanyloxy)heptadecan-3-one
• 英文别名: tert-butyl N-[(2S)-1-[tert-butyl(dimethyl)silyl]oxy-3-oxoheptadecan-2-yl]carbamate
• CAS: 693288-24-3
• 化学式: C₂₈H₅₇NO₄Si
• 分子量: 499.85
• InChiKey: HNXBWZRLXOVLEX-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.56
• 重原子数：
  34
• 可旋转键数：
  21
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S)-2-(t-butoxycarbonylamino)-1-(t-butyldimethylsilanyloxy)heptadecan-3-one 在 lithium tri-t-butoxyaluminum hydride 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以94%的产率得到(2S,3R)-2-(t-butoxycarbonylamino)-1-(t-butyldimethylsilanyloxy)heptadecan-3-ol
  参考文献：
  名称：

  Straightforward Synthesis of Sphinganines via a Serine-derived Weinreb Amide

  摘要：

  Sphinganines can be synthesized in just three steps from easily prepared serine-derived Weinreb amide 4. Pre-deprotonation of the acidic (N-H and O-H) protons of 4 allows for its efficient conversion to amino ketones 5. Such ketones can be selectively reduced to either erythro- or threo-sphinganines. Partially protected sphinganines 11 are also readily accessible in five steps from 4. Thus, Weinreb amide 4 represents one of the most versatile templates described to date for sphinganine synthesis.

  DOI：

  10.1021/jo030355b
• 作为产物：
  描述：

  N-甲氧基-N-甲基-N2-{[(2-甲基-2-丙基)氧基]羰基}-L-丝氨酰胺 在 咪唑 、 4-二甲氨基吡啶 、 叔丁基锂 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (2S)-2-(t-butoxycarbonylamino)-1-(t-butyldimethylsilanyloxy)heptadecan-3-one
  参考文献：
  名称：

  Straightforward Synthesis of Sphinganines via a Serine-derived Weinreb Amide

  摘要：

  Sphinganines can be synthesized in just three steps from easily prepared serine-derived Weinreb amide 4. Pre-deprotonation of the acidic (N-H and O-H) protons of 4 allows for its efficient conversion to amino ketones 5. Such ketones can be selectively reduced to either erythro- or threo-sphinganines. Partially protected sphinganines 11 are also readily accessible in five steps from 4. Thus, Weinreb amide 4 represents one of the most versatile templates described to date for sphinganine synthesis.

  DOI：

  10.1021/jo030355b

文献信息

• Straightforward Synthesis of Sphinganines via a Serine-derived Weinreb Amide
  作者：Regina C. So、Rachel Ndonye、Douglas P. Izmirian、Stewart K. Richardson、Robyn L. Guerrera、Amy R. Howell

  DOI：10.1021/jo030355b

  日期：2004.4.1

  Sphinganines can be synthesized in just three steps from easily prepared serine-derived Weinreb amide 4. Pre-deprotonation of the acidic (N-H and O-H) protons of 4 allows for its efficient conversion to amino ketones 5. Such ketones can be selectively reduced to either erythro- or threo-sphinganines. Partially protected sphinganines 11 are also readily accessible in five steps from 4. Thus, Weinreb amide 4 represents one of the most versatile templates described to date for sphinganine synthesis.