(2S,3R)-2-(t-butoxycarbonylamino)-1,3-heptadecanediol | 693288-30-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,3R)-2-(t-butoxycarbonylamino)-1,3-heptadecanediol
• 英文别名: tert-butyl N-[(2S,3R)-1,3-dihydroxyheptadecan-2-yl]carbamate
• CAS: 693288-30-1
• 化学式: C₂₂H₄₅NO₄
• 分子量: 387.604
• InChiKey: HXRXJYCCEJSTRT-VQTJNVASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  27
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  78.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3R)-2-(t-butoxycarbonylamino)-1,3-heptadecanediol 在 水 、 三氟乙酸 作用下， 反应 0.5h， 以98%的产率得到D-赤型鞘氨醇(C17碱)
  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 仲丁基氯化镁 、 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 反应 9.0h， 生成 (2S,3R)-2-(t-butoxycarbonylamino)-1,3-heptadecanediol
  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.