tert-butyl [(2S,3R,4R)-1,3,4-trihydroxyoctadecan-2-yl]carbamate | 1001429-10-2

• 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: tert-butyl [(2S,3R,4R)-1,3,4-trihydroxyoctadecan-2-yl]carbamate
• 英文别名: tert-butyl N-[(2S,3R,4R)-1,3,4-trihydroxyoctadecan-2-yl]carbamate
• CAS: 1001429-10-2
• 化学式: C₂₃H₄₇NO₅
• 分子量: 417.63
• InChiKey: QOKWGHLEDLDZTL-PWRODBHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  29
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  99
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl [(2S,3R,4R)-1,3,4-trihydroxyoctadecan-2-yl]carbamate 在 吡啶 、 对甲苯磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以50%的产率得到(2R,3R,4S)-4-(tert-butoxycarbonyl)amino-3-hydroxy-2-tetradecyltetrahydrofuran
  参考文献：
  名称：

  Synthesis and biological properties of Pachastrissamine (jaspine B) and diastereoisomeric jaspines

  摘要：

  The synthesis of isomeric jaspines (anhydro phytosphingosines), arising from intramolecular cyclization of the corresponding phytosphingosines with different con. gurations at C3 and C4 positions of the sphingoid backbone, is reported. Natural jaspine B is the most cytotoxic isomer on A549 cells and it induces cell death in a dose-dependent manner. The cytotoxicity of jaspine B has been correlated with a significant increase of intracellular dihydroceramides, which seem to play an active role in autophagy. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.11.026
• 作为产物：
  描述：

  (4S,5R,6R)-5-(tert-butyldimethylsilyloxy)-4-[(tert-butyldimethylsilyloxy)methyl]-2-phenyl-6-(tetradec-1-enyl)-5,6-dihydro-4H-1,3-oxazine 在 20% palladium hydroxide on charcoal 、 四丁基氟化铵 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 13.0h， 生成 tert-butyl [(2S,3R,4R)-1,3,4-trihydroxyoctadecan-2-yl]carbamate
  参考文献：
  名称：

  基于手性 1,3-恶嗪合成的 D-木-和 D-阿拉伯-植物鞘氨醇的全合成

  摘要：

  利用手性恶嗪实现了一种高效、立体控制且短的合成方法，用于制备 D-木-和 D-阿拉伯-植物鞘氨醇。该策略的关键特征是由钯 (0) 和分子间烯烃交叉复分解反应催化的立体选择性分子内恶嗪形成。

  DOI：

  10.1002/ejoc.201200064

文献信息

• Syntheses and biological activities of KRN7000 analogues having aromatic residues in the acyl and backbone chains with varying stereochemistry
  作者：Jeong-Ju Park、Ji Hyung Lee、Kyung-Chang Seo、Gabriel Bricard、Manjunatha M. Venkataswamy、Steven A. Porcelli、Sung-Kee Chung

  DOI：10.1016/j.bmcl.2009.12.103

  日期：2010.2

  effort to understand the structure–activity relationships, we have carried out syntheses of 26 new KRN7000 analogues incorporating aromatic residues in either or both side chains. Structural variations of the phytosphingosine moiety also include varying stereochemistry at C3 and C4, and 4-deoxy and 3,4-dideoxy versions. Their biological activities are described.

  KRN7000 是 APC 的 CD1d 蛋白的重要配体，KRN7000/CD1d 复合物可以刺激 NKT 细胞释放多种生物活性细胞因子。为了理解结构-活性关系，我们合成了 26 个新的 KRN7000 类似物，它们在一个或两个侧链中加入了芳香族残基。植物鞘氨醇部分的结构变化还包括 C3 和 C4 以及 4-脱氧和 3,4-双脱氧形式的不同立体化学。描述了它们的生物活性。
• Synthesis and preliminary antifungal evaluation of a library of phytosphingolipid analogues
  作者：David Mormeneo、Josefina Casas、Amadeu Llebaria、Antonio Delgado

  DOI：10.1039/b709421c

  日期：——

  A library of 64 phytosphingolipid analogues resulting from the systematic variation of the C1, C3, C4, and the N-acyl moiety of phytosphingosine (PHS) has been prepared from common scaffolds derived from the chiral pool and Sharpless asymmetric dihydroxylation reactions. Library members have been evaluated as growth inhibitors of the yeast Saccaromyces cerevisiae. In addition, 1-amino-N-pivaloyl PHS analogues were also tested as IPC synthase inhibitors, in comparison with the natural product khafrefungin.

  已制备出一个由64种植物鞘氨醇类类似物组成的库，这些类似物是通过系统改变植物鞘氨醇（PHS）的C1、C3、C4和N-酰基基团而获得的，采用了源自手性池和Sharpless不对称二醇化反应的公共骨架。该库的成员作为酵母酿酒酵母（Saccaromyces cerevisiae）的生长抑制剂进行了评估。此外，还测试了1-氨基-N-哌喹酰PHS类似物，作为IPC合成酶抑制剂，并与天然产物khafrefungin进行比较。
• Stereoselective Divergent Synthesis of Four Diastereomers of Pachastrissamine (Jaspine B)
  作者：Yuji Yoshimitsu、Shinsuke Inuki、Shinya Oishi、Nobutaka Fujii、Hiroaki Ohno

  DOI：10.1021/jo1005284

  日期：2010.6.4

  A divergent short synthesis of four diastereomers of pachastrissamine was achieved. Natural pachastrissamine was synthesized through bis-tosylation of the common intermediate and cyclization. 2-epi-Pachastrissamine was obtained by monotosylation and spontaneous cyclization of D-ribo-phytosphingosine derivative. By use of regio- and stereospecific ring-opening reaction of the orthoester assisted by a Bee group as a key step, 3-epi- and 2,3-epi-pachastrissamines were synthesized. The three stereogenic centers of all the diastereomers were constructed by using Garner's aldehyde as the sole chiral source.
• Total Syntheses of D-xylo- and D-arabino-Phytosphingosine Based on the Syntheses of Chiral 1,3-Oxazines
  作者：Yu Mu、Tian Jin、Gun-Woo Kim、Jin-Seok Kim、Sung-Soo Kim、Yong-Shou Tian、Chang-Young Oh、Won-Hun Ham

  DOI：10.1002/ejoc.201200064

  日期：2012.5

  An efficient, stereocontrolled, and short synthetic method for the preparation D-xylo- and D-arabino-phytosphingsine was achieved utilizing chiral oxazines. The key features of this strategy are the stereoselective intramolecular oxazine formation catalyzed by palladium(0) and an intermolecular olefin cross-metathesis reaction.

  利用手性恶嗪实现了一种高效、立体控制且短的合成方法，用于制备 D-木-和 D-阿拉伯-植物鞘氨醇。该策略的关键特征是由钯 (0) 和分子间烯烃交叉复分解反应催化的立体选择性分子内恶嗪形成。
• Synthesis and biological properties of Pachastrissamine (jaspine B) and diastereoisomeric jaspines
  作者：Daniel Canals、David Mormeneo、Gemma Fabriàs、Amadeu Llebaria、Josefina Casas、Antonio Delgado

  DOI：10.1016/j.bmc.2008.11.026

  日期：2009.1

  The synthesis of isomeric jaspines (anhydro phytosphingosines), arising from intramolecular cyclization of the corresponding phytosphingosines with different con. gurations at C3 and C4 positions of the sphingoid backbone, is reported. Natural jaspine B is the most cytotoxic isomer on A549 cells and it induces cell death in a dose-dependent manner. The cytotoxicity of jaspine B has been correlated with a significant increase of intracellular dihydroceramides, which seem to play an active role in autophagy. (c) 2008 Elsevier Ltd. All rights reserved.