tert-butyl ((2R,3S,4S)-3-(benzyloxy)-1,4-dihydroxyoctadecan-2-yl)carbamate | 1338778-33-8

• 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 ((2R,3S,4S)-3-(benzyloxy)-1,4-dihydroxyoctadecan-2-yl)carbamate
• 英文别名: tert-butyl [(2R,3S,4S)-1,3,4-trihydroxyoctadecan-2-yl]carbamate；tert-butyl N-[(2R,3S,4S)-1,3,4-trihydroxyoctadecan-2-yl]carbamate
• CAS: 1338778-33-8
• 化学式: C₂₃H₄₇NO₅
• 分子量: 417.63
• InChiKey: QOKWGHLEDLDZTL-HKBOAZHASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.69
• 重原子数：
  29.0
• 可旋转键数：
  17.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  99.02
• 氢给体数：
  4.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  tert-butyl ((2R,3S,4S)-3-(benzyloxy)-1,4-dihydroxyoctadecan-2-yl)carbamate 在 三甲胺盐酸盐 、 三乙胺 、 对甲苯磺酰氯 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (2S,3S,4R)-2-tetradecyl-4-aminotetrahydrofuran-3-ol
  参考文献：
  名称：

  Pachastrissamine (jaspine B) and its stereoisomers inhibit sphingosine kinases and atypical protein kinase C

  摘要：

  Sphingosine kinases (SphKs) are oncogenic enzymes that regulate the critical balance between ceramide and sphingosine-1-phosphate. Much effort has been dedicated to develop inhibitors against these enzymes. Naturally occurring pachastrissamine (jaspine B) and all its stereoisomers were prepared and evaluated for their inhibitory effects against SphKs. All eight stereoisomers exhibited moderate to potent inhibitory activity against SphK1 and SphK2. Inhibitory effects were profiled against protein kinase C (PKC) isoforms by in vitro experiments. Atypical PKCs (PKC zeta and PKC iota) were inhibited by several pachastrissamine stereoisomers. The improved activity over N,N-dimethylsphingosine suggests that the cyclic scaffold in pachastrissamines facilitates potential favorable interactions with SphKs and PKCs. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.061
• 作为产物：
  描述：

  tert-butyl (S,Z)-2,2-dimethyl-4-(hexadec-1'-en-1'-yl)oxazolidine-3-carboxylate 在 咪唑 、 4-二甲氨基吡啶 、 四氧化锇 、 三氟化硼乙醚 、 四丁基氟化铵 、 对甲苯磺酸 、 N-甲基吗啉氧化物 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 9.0h， 生成 tert-butyl ((2R,3S,4S)-3-(benzyloxy)-1,4-dihydroxyoctadecan-2-yl)carbamate
  参考文献：
  名称：

  Pachastrissamine (jaspine B) and its stereoisomers inhibit sphingosine kinases and atypical protein kinase C

  摘要：

  Sphingosine kinases (SphKs) are oncogenic enzymes that regulate the critical balance between ceramide and sphingosine-1-phosphate. Much effort has been dedicated to develop inhibitors against these enzymes. Naturally occurring pachastrissamine (jaspine B) and all its stereoisomers were prepared and evaluated for their inhibitory effects against SphKs. All eight stereoisomers exhibited moderate to potent inhibitory activity against SphK1 and SphK2. Inhibitory effects were profiled against protein kinase C (PKC) isoforms by in vitro experiments. Atypical PKCs (PKC zeta and PKC iota) were inhibited by several pachastrissamine stereoisomers. The improved activity over N,N-dimethylsphingosine suggests that the cyclic scaffold in pachastrissamines facilitates potential favorable interactions with SphKs and PKCs. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.061

文献信息

• Stereoselective Synthesis of β-Amino Ynones by the Addition of Alkynones to Nonracemic Sulfinimines: Formal Total Synthesis of <scp>l</scp>-<i>Xylo</i> and <scp>l</scp>-<i>Arabino</i> Phytosphingosines
  作者：Polimera Obula Reddy、Arava Amaranadha Reddy、Kavirayani R. Prasad

  DOI：10.1021/acs.joc.9b02938

  日期：2020.2.21

  sulfinimines furnished the corresponding β-sulfinamido ynones in a very good yield and diastereoselectivity. The formed ynones serve as precursors amenable for the synthesis of bioactive compounds. This has been illustrated in the synthesis of l-xylo and l-arabino phytosphingosines.

  将由炔酮得到的甲硅烷基烯醇醚加到亚磺胺中，以非常好的收率和非对映选择性提供了相应的β-亚磺酰胺基炔酮。形成的炔酮用作适于合成生物活性化合物的前体。在1-xylo和1-阿拉伯糖基植物鞘氨醇的合成中已经说明了这一点。