(2S,3R)-2-(N-tert-butoxycarbonyl)amino-1-tert-butyldimethylsilanyloxyoctadecan-3-ol | 872356-70-2

• 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,3R)-2-(N-tert-butoxycarbonyl)amino-1-tert-butyldimethylsilanyloxyoctadecan-3-ol
• 英文别名: tert-butyl N-[(2S,3R)-1-[tert-butyl(dimethyl)silyl]oxy-3-hydroxyoctadecan-2-yl]carbamate
• CAS: 872356-70-2
• 化学式: C₂₉H₆₁NO₄Si
• 分子量: 515.893
• InChiKey: RPCMFKMCFJPBLC-IZZNHLLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.74
• 重原子数：
  35
• 可旋转键数：
  22
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 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-butyldimethylsilanyloxyoctadecan-3-ol 在 水 、 四丁基碘化铵 、 sodium hydride 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (2S,3R)-2-amino-3-benzyloxyoctadecan-1-ol
  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 tri(cycloxexyl)phosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]ruthenium(IV) dichloride 咪唑 、 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.59h， 生成 (2S,3R)-2-(N-tert-butoxycarbonyl)amino-1-tert-butyldimethylsilanyloxyoctadecan-3-ol
  参考文献：
  名称：

  通过烯烃交叉复分解的多功能合成方法，用于鞘脂和功能化鞘氨醇衍生物。

  摘要：

  通过烯烃交叉复分解反应的两种组合，建立了一种高效且通用的合成各种鞘脂的方法，如鞘磷脂，神经酰胺，鞘氨醇，1-磷酸鞘氨醇和功能化鞘氨醇衍生物。一个反应是在相同的烯烃部分与合适的氨基醇之间，它们从N-Boc-L-丝氨酸开始制备，另一个反应在合适的烯烃与相同的氨基醇之间。[反应：请参见文字]。

  DOI：

  10.1021/ol062258l

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.
• Versatile Synthetic Method for Sphingolipids and Functionalized Sphingosine Derivatives via Olefin Cross Metathesis
  作者：Tetsuya Yamamoto、Hiroko Hasegawa、Toshikazu Hakogi、Shigeo Katsumura

  DOI：10.1021/ol062258l

  日期：2006.11.1

  and versatile method for the synthesis of various sphingolipids, such as sphingomyelin, ceramide, sphingosine, sphingosine 1-phosphate, and functionalized sphingosine derivatives, was established by two types of combinations of the olefin cross metathesis reaction. One reaction was between the same olefin part and appropriate amino alcohols, which were prepared starting from N-Boc-L-serine, and the other

  通过烯烃交叉复分解反应的两种组合，建立了一种高效且通用的合成各种鞘脂的方法，如鞘磷脂，神经酰胺，鞘氨醇，1-磷酸鞘氨醇和功能化鞘氨醇衍生物。一个反应是在相同的烯烃部分与合适的氨基醇之间，它们从N-Boc-L-丝氨酸开始制备，另一个反应在合适的烯烃与相同的氨基醇之间。[反应：请参见文字]。