N-tert-butoxycarbonyl (4S)-4-[1'-(3''-dodecylphenyl)hydroxymethyl]-2,2-dimethyl-1,3-oxazolidine | 709026-54-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-tert-butoxycarbonyl (4S)-4-[1'-(3''-dodecylphenyl)hydroxymethyl]-2,2-dimethyl-1,3-oxazolidine
• 英文别名: N-tert-butoxycarbonyl (4S)-4-[1'-(3"-dodecylphenyl)hydroxymethyl]-2,2-dimethyl-1,3-oxazolidine；tert-butyl (4S)-4-[1-(3-dodecylphenyl)hydroxymethyl]-2,2-dimethyl-3-oxazolinecarboxylate
• CAS: 709026-54-0
• 化学式: C₂₉H₄₉NO₄
• 分子量: 475.712
• InChiKey: QBSZEMKZANPTCN-PMCHYTPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.56
• 重原子数：
  34.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  59.0
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-tert-butoxycarbonyl (4S)-4-[1'-(3''-dodecylphenyl)hydroxymethyl]-2,2-dimethyl-1,3-oxazolidine 在 吡啶 、 四溴化碳 、 二异丁基氢化铝 、 溶剂黄146 、 pyridinium chlorochromate 、 lithium chloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 dimethyl (2S,3R)-2-(tert-butoxycarbonylamino)-3-(hydroxy-3-dodecylphenyl)prop-1-ylphosphate
  参考文献：
  名称：

  Syntheses of sphingosine-1-phosphate analogues and their interaction with EDG/S1P receptors

  摘要：

  Sphingosine-I-phosphate (SIP) is an important regulator of a wide variety of biological processes acting as an endogenous ligand to EDG/S1P receptors. In an effort to establish structure-activity relationship between EDG/S1P and ligands, we report herein homology modeling study of EDG-1/S1P(1), syntheses of S I P analogues, and cell based binding affinity study for EDG/S1P receptors. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.001
• 作为产物：
  描述：

  1-bromo-3-dodecylbenzene 、 3-反-溴碳-2,2'-二甲基氧酸酯 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 N-tert-butoxycarbonyl (4S)-4-[1'-(3''-dodecylphenyl)hydroxymethyl]-2,2-dimethyl-1,3-oxazolidine
  参考文献：
  名称：

  Syntheses of sphingosine-1-phosphate analogues and their interaction with EDG/S1P receptors

  摘要：

  Sphingosine-I-phosphate (SIP) is an important regulator of a wide variety of biological processes acting as an endogenous ligand to EDG/S1P receptors. In an effort to establish structure-activity relationship between EDG/S1P and ligands, we report herein homology modeling study of EDG-1/S1P(1), syntheses of S I P analogues, and cell based binding affinity study for EDG/S1P receptors. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.001

文献信息

• Practical Syntheses of Sphingosine-1-Phosphate and Analogues
  作者：Hans-Ulrich Reissig、Virginie Blot、Ulrich Jacquemard、Burkhard Kleuser

  DOI：10.1055/s-0028-1083373

  日期：——

  including proliferation, survival, and migration. For this reason the stereoselective syntheses of S1P and analogues are of great interest. Based on l-serine as source of chirality we achieved practical routes to prepare S1P (1) and the aryl group containing analogues 3 and 4 in fair amounts. The crucial stages of the syntheses are: introduction of the required side chain by addition of appropriate organometallics

  鞘氨醇-1-磷酸酯（S1P，1）是一种生物活性鞘脂代谢产物，涉及多种关键细胞过程，包括增殖，存活和迁移。因此，S1P及其类似物的立体选择性合成引起人们极大的兴趣。基于1-丝氨酸作为手性来源，我们获得了制备S1P（1）和含有相当量类似物3和4的芳基的实用途径。合成的关键步骤是：通过向Garner醛中添加适当的有机金属来引入所需的侧链，并将伯醇转化为相应的磷酸盐。 磷酸盐-氨基醇-脂质-有机金属试剂-鞘氨醇衍生物
• Synthesis of Ceramide Analogues Having the C(4)−C(5) Bond of the Long-Chain Base as Part of an Aromatic or Heteroaromatic System
  作者：Jiong Chun、Linli He、Hoe-Sup Byun、Robert Bittman

  DOI：10.1021/jo001227f

  日期：2000.11.1

  preparation of aryl and heteroaryl ceramide analogues 2 and 3. The first route involves the addition of an aryllithium or a heteroaryllithium reagent (7a or 25a, respectively) to the L-serine-derived aldehyde 4, followed by hydrolysis of the oxazolidine, liberation of the amino group, and N-acylation. The second route, which was used to prepare arylceramide analogue 2 in eight steps and 28% overall yield starting

  描述了两种有效的和立体选择性的方法，用于制备芳基和杂芳基神经酰胺类似物2和3。第一种方法涉及向L-丝氨酸衍生的醛4中添加芳基锂或杂芳基锂试剂（分别为7a或25a）。然后是恶唑烷的水解，氨基的释放和N-酰化。第二种方法是使用八步制备芳基神经酰胺类似物2的方法，从3-溴苯甲醛开始，总产率为28％，该方法利用Heck反应生成（E）-α，β-不饱和酯16，然后由-催化的不对称二羟基化反应用于在C-2和C-3处引入所需的手性。与叠氮化钠的区域选择性α-叠氮α-O-nosyl-β-羟基酯18，然后由LiAlH（4）还原叠氮基和酯基以及N-酰化，