2,2-Dimethyl-propionic acid (E)-(2S,3R)-2-tert-butoxycarbonylamino-3-hydroxy-octadec-4-enyl ester | 342649-71-2

• 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: 2,2-Dimethyl-propionic acid (E)-(2S,3R)-2-tert-butoxycarbonylamino-3-hydroxy-octadec-4-enyl ester
• 英文别名: (2S,3R,E)-2-((tert-butoxycarbonyl)amino)-3-hydroxyoctadec-4-en-1-yl pivalate；[(E,2S,3R)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]octadec-4-enyl] 2,2-dimethylpropanoate
• CAS: 342649-71-2
• 化学式: C₂₈H₅₃NO₅
• 分子量: 483.733
• InChiKey: FNDFSKJECZVDNY-UVAUYHEJSA-N

物化性质

• 溶解度：
  溶于二氯甲烷、乙酸乙酯、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  34
• 可旋转键数：
  21
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2-Dimethyl-propionic acid (E)-(2S,3R)-2-tert-butoxycarbonylamino-3-hydroxy-octadec-4-enyl ester 在 咪唑 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 tert-butyl (2S,3R,E)-2-(tert-butyldimethylsiloxy)-1-hydroxyoctadec-4-en-2-ylcarbamate
  参考文献：
  名称：

  Sphingomyelin analogues as inhibitors of sphingomyelinase

  摘要：

  To search for neutral sphingomyelinase inhibitors we designed and synthesized hydrolytically stable analogues of sphingomyelin. The novel compounds 8 and 9 which were replaced the phosphodiester moiety of sphingomyelin with the carbamate moiety showed inhibitory activity with an IC50 value of muM on neutral sphingomyelinase in rat brain microsomes. Compound 8i showed a selective neutral sphingomyelinase inhibitory activity. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00360-3
• 作为产物：
  描述：

  三甲基乙酰氯 、 N-叔丁氧羰基-赤式-鞘氨醇 在 吡啶 作用下， 以91%的产率得到2,2-Dimethyl-propionic acid (E)-(2S,3R)-2-tert-butoxycarbonylamino-3-hydroxy-octadec-4-enyl ester
  参考文献：
  名称：

  Sphingomyelin analogues as inhibitors of sphingomyelinase

  摘要：

  To search for neutral sphingomyelinase inhibitors we designed and synthesized hydrolytically stable analogues of sphingomyelin. The novel compounds 8 and 9 which were replaced the phosphodiester moiety of sphingomyelin with the carbamate moiety showed inhibitory activity with an IC50 value of muM on neutral sphingomyelinase in rat brain microsomes. Compound 8i showed a selective neutral sphingomyelinase inhibitory activity. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00360-3

文献信息

• Sphingomyelin analogues as inhibitors of sphingomyelinase
  作者：Minoru Taguchi、Kikuo Sugimoto、Ken-ichi Goda、Tomoko Akama、Kyoko Yamamoto、Taizo Suzuki、Yasumitsu Tomishima、Mariko Nishiguchi、Koshi Arai、Kenzo Takahashi、Takeo Kobori

  DOI：10.1016/s0960-894x(03)00360-3

  日期：2003.6

  To search for neutral sphingomyelinase inhibitors we designed and synthesized hydrolytically stable analogues of sphingomyelin. The novel compounds 8 and 9 which were replaced the phosphodiester moiety of sphingomyelin with the carbamate moiety showed inhibitory activity with an IC50 value of muM on neutral sphingomyelinase in rat brain microsomes. Compound 8i showed a selective neutral sphingomyelinase inhibitory activity. (C) 2003 Elsevier Science Ltd. All rights reserved.