(2R,3R,4S)-4-acetamido-2-tetradecyltetrahydrofuran-3-yl acetate | 1219017-13-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢呋喃
• 英文名称: (2R,3R,4S)-4-acetamido-2-tetradecyltetrahydrofuran-3-yl acetate
• 英文别名: [(2R,3R,4S)-4-acetamido-2-tetradecyloxolan-3-yl] acetate
• CAS: 1219017-13-6
• 化学式: C₂₂H₄₁NO₄
• 分子量: 383.572
• InChiKey: LUFXSTBCUCLTGY-BHDDXSALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  27
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2R,3R,4S)-4-amino-2-tetradecyltetrahydrofuran-3-ol hydrochloride 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 18.5h， 以85%的产率得到(2R,3R,4S)-4-acetamido-2-tetradecyltetrahydrofuran-3-yl acetate
  参考文献：
  名称：

  Total synthesis of (−)-jaspine B and its 4-epi-analogue from d-xylose

  摘要：

  The total synthesis of the HCl salts of (-)-jaspine B ent-1 and its 4-epi-congener ent-4 was accomplished starting from the common template 13 derived from D-xylose. The cornerstone of our synthesis was [3,3]-heterosigmatropic rearrangements, which effectively provided scaffolds with a chiral amino group. A subsequent Wittig olefination installed a C-14 alkyl side chain and acid-mediated ring-closing reaction established the tetrahydrofuran core. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.04.002

文献信息

• Stereoselective Synthesis and Biological Studies of the C2 and C3 Epimer and the Enantiomer of Pachastrissamine (Jaspine B)
  作者：B. Rao、G. Jayachitra、N. Sudhakar、Ravi Anchoori、Sayantani Roy、Rajkumar Banerjee

  DOI：10.1055/s-0029-1217096

  日期：2010.1

  The synthesis of the C2 and C3 epimer and also the enantiomer of jaspine B from d-glucose is reported. The cytotoxicity of these isomers along with jaspine B and its C2 epimer on MCF7 cells has been correlated with commercially available anticancer drug Epirubicin.

  据报道，研究人员从 d-葡萄糖中合成了天麻素 B 的 C2 和 C3 外比体以及对映体。这些异构体以及雅司平 B 及其 C2 表亚体对 MCF7 细胞的细胞毒性与市售抗癌药物表柔比星相关。