(2S,3R)-2-(N-tert-butoxycarbonyl)amino-1-tert-butyldimethylsilanyloxy-3-benzyloxyoctadecane | 872356-71-3

• 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: (2S,3R)-2-(N-tert-butoxycarbonyl)amino-1-tert-butyldimethylsilanyloxy-3-benzyloxyoctadecane
• 英文别名: tert-butyl N-[(2S,3R)-1-[tert-butyl(dimethyl)silyl]oxy-3-phenylmethoxyoctadecan-2-yl]carbamate
• CAS: 872356-71-3
• 化学式: C₃₆H₆₇NO₄Si
• 分子量: 606.018
• InChiKey: JJZLFBFFUKCHON-JHOUSYSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.97
• 重原子数：
  42
• 可旋转键数：
  25
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3R)-2-(N-tert-butoxycarbonyl)amino-1-tert-butyldimethylsilanyloxy-3-benzyloxyoctadecane 在 吡啶 、 水 、 三氟乙酸 作用下， 反应 22.0h， 生成 (2S,3R)-3-O-benzyl-2-(N-hexacosanoylamino)octadecan-1,3-diol
  参考文献：
  名称：

  Synthesis and Evaluation of Sphinganine Analogues of KRN7000 and OCH

  摘要：

  The phytosphingosine-containing alpha-galactosylceramides (alpha-GalCers), KRN7000 and OCH, have been shown to activate NKT cells via interaction with CD1d, a member of the CD1 family of antigen presenting proteins. Evidence from KRN7000 stimulation of NKT cells suggests that alpha-GalCers may have applications in the treatment or prevention of a range of viral, bacterial, and autoimmune conditions. Moreover, OCH, a truncated analogue of KRN7000, appears to induce a T(H)2 bias, which could have implications for the treatment of autoimmune and inflammatory conditions. We have prepared the direct sphinganine-containing analogues of KRN7000 and OCH, 1 and 2, and found them to be comparable in activity to the parent compounds in inducing the release of IL-2, IL-4, and IFN gamma. In addition, compound 2 leads to a cytokine bias similar to that seen with OCH. This is significant because sphinganines are more easily accessed than phytosphingosines, which should facilitate SAR studies.

  DOI：

  10.1021/jo051147h
• 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 、 仲丁基氯化镁 、 四丁基碘化铵 、 sodium hydride 、 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 (2S,3R)-2-(N-tert-butoxycarbonyl)amino-1-tert-butyldimethylsilanyloxy-3-benzyloxyoctadecane
  参考文献：
  名称：

  Synthesis and Evaluation of Sphinganine Analogues of KRN7000 and OCH

  摘要：

  The phytosphingosine-containing alpha-galactosylceramides (alpha-GalCers), KRN7000 and OCH, have been shown to activate NKT cells via interaction with CD1d, a member of the CD1 family of antigen presenting proteins. Evidence from KRN7000 stimulation of NKT cells suggests that alpha-GalCers may have applications in the treatment or prevention of a range of viral, bacterial, and autoimmune conditions. Moreover, OCH, a truncated analogue of KRN7000, appears to induce a T(H)2 bias, which could have implications for the treatment of autoimmune and inflammatory conditions. We have prepared the direct sphinganine-containing analogues of KRN7000 and OCH, 1 and 2, and found them to be comparable in activity to the parent compounds in inducing the release of IL-2, IL-4, and IFN gamma. In addition, compound 2 leads to a cytokine bias similar to that seen with OCH. This is significant because sphinganines are more easily accessed than phytosphingosines, which should facilitate SAR studies.

  DOI：

  10.1021/jo051147h

文献信息

• Synthesis and Evaluation of Sphinganine Analogues of KRN7000 and OCH
  作者：Rachel M. Ndonye、Douglas P. Izmirian、Matthew F. Dunn、Karl O. A. Yu、Steven A. Porcelli、Archana Khurana、Mitchell Kronenberg、Stewart K. Richardson、Amy R. Howell

  DOI：10.1021/jo051147h

  日期：2005.12.1

  The phytosphingosine-containing alpha-galactosylceramides (alpha-GalCers), KRN7000 and OCH, have been shown to activate NKT cells via interaction with CD1d, a member of the CD1 family of antigen presenting proteins. Evidence from KRN7000 stimulation of NKT cells suggests that alpha-GalCers may have applications in the treatment or prevention of a range of viral, bacterial, and autoimmune conditions. Moreover, OCH, a truncated analogue of KRN7000, appears to induce a T(H)2 bias, which could have implications for the treatment of autoimmune and inflammatory conditions. We have prepared the direct sphinganine-containing analogues of KRN7000 and OCH, 1 and 2, and found them to be comparable in activity to the parent compounds in inducing the release of IL-2, IL-4, and IFN gamma. In addition, compound 2 leads to a cytokine bias similar to that seen with OCH. This is significant because sphinganines are more easily accessed than phytosphingosines, which should facilitate SAR studies.