(S)-tert-butyl 4-((S,E)-1-hydroxytridec-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate | 524730-23-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (S)-tert-butyl 4-((S,E)-1-hydroxytridec-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate
• 英文别名: tert-butyl (4S)-4-[(E,1S)-1-hydroxytridec-2-enyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 524730-23-2
• 化学式: C₂₃H₄₃NO₄
• 分子量: 397.599
• InChiKey: FAJRALDLRGTAFH-KEENPFPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  28
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl 4-((S,E)-1-hydroxytridec-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate 在 溶剂黄146 作用下， 反应 5.0h， 生成 ((E)-(1S,2S)-2-Hydroxy-1-hydroxymethyl-tetradec-3-enyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis and biological properties of novel sphingosine derivatives

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2004.12.010
• 作为产物：
  描述：

  (1S/R)-1-[(4S)-N-(tert-Butoxycarbonyl)-2,2-dimethyloxazolidin-4-yl]prop-2-en-1-ol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 sodium tetrahydroborate 、 cerium(III) chloride 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 4.08h， 生成 (S)-tert-butyl 4-((R,E)-1-hydroxytridec-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate 、 (S)-tert-butyl 4-((S,E)-1-hydroxytridec-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate
  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