N-[(3E)(1S,2R)-2-hydroxy-1-(hydroxymethyl)tetradec-3-enyl](tert-butoxy)carboxamide | 849215-49-2

• 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: N-[(3E)(1S,2R)-2-hydroxy-1-(hydroxymethyl)tetradec-3-enyl](tert-butoxy)carboxamide
• 英文别名: tert-butyl ((2S,3R,E)-1,3-dihydroxypentadec-4-en-2-yl)carbamate
• CAS: 849215-49-2
• 化学式: C₂₀H₃₉NO₄
• 分子量: 357.534
• InChiKey: XPUCQIKDMFCEJW-KRWOKUGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  25.0
• 可旋转键数：
  13.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  78.79
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-[(3E)(1S,2R)-2-hydroxy-1-(hydroxymethyl)tetradec-3-enyl](tert-butoxy)carboxamide 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 D-赤型鞘氨醇C-15
  参考文献：
  名称：

  Ceramides: Branched alkyl chains in the sphingolipid siblings of diacylglycerol improve biological potency

  摘要：

  The synthesis of a small number of ceramide analogues containing a combination of linear and highly branched alkyl chains on either the D-sphingosine or the N-acyl core of the molecule is reported. Regardless of location, the presence of the branched chain improves potency relative to the positive control, C2 ceramide; however, the most potent compound (4) has the branched side chain as part of the D-sphingosine core. The induction of apoptosis by 4 in terms of Annexin V binding and DiOC(6) labeling was superior to that achieved with C2 ceramide. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.01.005
• 作为产物：
  描述：

  (S)-tert-butyl 4-((R,E)-1-hydroxytridec-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以79%的产率得到N-[(3E)(1S,2R)-2-hydroxy-1-(hydroxymethyl)tetradec-3-enyl](tert-butoxy)carboxamide
  参考文献：
  名称：

  A diversity oriented synthesis of d - erythro -sphingosine and siblings

  摘要：

  An efficient building block-based synthetic protocol has been developed for the synthesis of 3-keto-sphingoids with various chain lengths using cross metathesis of a Garner's aldehyde-derived alpha,beta-unsaturated ketone as the key step. Stereoselective reduction of the biomimetic precursors thus obtained provided D-elythro-sphingosine and truncated anaogues in good overall yields. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2017.08.006

文献信息

• Synthesis and biological properties of novel sphingosine derivatives
  作者：Teiichi Murakami、Kiyotaka Furusawa、Tadakazu Tamai、Kazuyoshi Yoshikai、Masazumi Nishikawa

  DOI：10.1016/j.bmcl.2004.12.010

  日期：2005.2

  Sphingosine-1-phosphate (S-1P) derivatives such as threo-(2S,3S)-analogues, which are C-3 stereoisomers of natural erythro-(2S,3R)-S-1P, have been synthesized starting from L-serine or (IS,2S)-2-amino-1-aryl-1,3-propanediols (6). threo-(IS,2R)2-Amino-1-aryl-3-bromopropanols (HBr salt) have also been prepared from 6. The threo-S-1Ps and the threo-amino-bromide derivatives have shown potent inhibitory activity against Ca2+ ion mobilization in HL60 cells induced by erythro-S-1P, suggesting that these compounds would compete with cell surface EDG/S1P receptors. (C) 2004 Elsevier Ltd. All rights reserved.