(2R,3R)-[3-(4'-methoxy-benzyloxymethyl)-1,4-dioxa-spiro[4.4]non-2-yl]-methanol | 607358-63-4

• 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: (2R,3R)-[3-(4'-methoxy-benzyloxymethyl)-1,4-dioxa-spiro[4.4]non-2-yl]-methanol
• 英文别名: [(2R,3R)-3-[(4-methoxyphenyl)methoxymethyl]-1,4-dioxaspiro[4.4]nonan-2-yl]methanol
• CAS: 607358-63-4
• 化学式: C₁₇H₂₄O₅
• 分子量: 308.375
• InChiKey: AKQFYPFTQZUIGC-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R)-[3-(4'-methoxy-benzyloxymethyl)-1,4-dioxa-spiro[4.4]non-2-yl]-methanol 在 四氮唑 、 盐酸 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (2-{benzyloxy-[(2R,3R)-2,3-dihydroxy-4-(4'-methoxybenzyloxymethyl)-butoxy]-phosphoryloxy}-ethyl)-carbamic acid benzyl ester
  参考文献：
  名称：

  Synthesis of Hybrid Lipid Probes:  Derivatives of Phosphatidylethanolamine-Extended Phosphatidylinositol 4,5-Bisphosphate (Pea-PIP₂)

  摘要：

  The total asymmetric synthesis of a novel hybrid lipid possessing a 2,3-diacylthreitol backbone, rather than a 1,2-diacylglycerol backbone, is described. The title compound, Pea-PIP2, possesses a phosphatidylethanolamine (PE) headgroup at the 1-position and a phosphatidylinositol 4,5-bisphosphate (Ptdlns(4,5)P-2) headgroup, at the 4-position. Reporters (biotin, fluorophores, spin label) were covalently attached to the free amino group of the PE, such that these reporters were targeted to the lipid-water interface. The diacyl moieties allow incorporation of Pea-PIP2 into a lipid bilayer, while the PtdIns(4,5)P-2 moiety in the aqueous layer was specifically recognized by PtdIns(4,5)P-2-specific binding proteins.

  DOI：

  10.1021/jo011185a
• 作为产物：
  描述：

  (2S,3S)-1,4-dioxa-spiro[4.4]nonane-2,3-dicarboxylic acid diethyl ester 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.0h， 生成 (2R,3R)-[3-(4'-methoxy-benzyloxymethyl)-1,4-dioxa-spiro[4.4]non-2-yl]-methanol
  参考文献：
  名称：

  Synthesis of Hybrid Lipid Probes:  Derivatives of Phosphatidylethanolamine-Extended Phosphatidylinositol 4,5-Bisphosphate (Pea-PIP₂)

  摘要：

  The total asymmetric synthesis of a novel hybrid lipid possessing a 2,3-diacylthreitol backbone, rather than a 1,2-diacylglycerol backbone, is described. The title compound, Pea-PIP2, possesses a phosphatidylethanolamine (PE) headgroup at the 1-position and a phosphatidylinositol 4,5-bisphosphate (Ptdlns(4,5)P-2) headgroup, at the 4-position. Reporters (biotin, fluorophores, spin label) were covalently attached to the free amino group of the PE, such that these reporters were targeted to the lipid-water interface. The diacyl moieties allow incorporation of Pea-PIP2 into a lipid bilayer, while the PtdIns(4,5)P-2 moiety in the aqueous layer was specifically recognized by PtdIns(4,5)P-2-specific binding proteins.

  DOI：

  10.1021/jo011185a

文献信息

• Total Synthesis of (+)-Amphidinolide A. Assembly of the Fragments
  作者：Barry M. Trost、Stephen T. Wrobleski、John D. Chisholm、Paul E. Harrington、Michael Jung

  DOI：10.1021/ja0533646

  日期：2005.10.1

  The structure elucidation of (+)-amphidinolide A, a cytotoxic macrolide, has been accomplished by employing a combination of total synthesis and NMR spectroscopic analysis. Amphidinolide A possesses two skipped 1,4-diene subunits which are accessible by ruthenium-catalyzed alkene-alkyne couplings. Previous total syntheses had revealed that the reported structure was incorrect; therefore, to incorporate

  (+)-amphidinolide A（一种细胞毒性大环内酯）的结构解析已通过采用全合成和 NMR 光谱分析的组合完成。Amphidinolide A 具有两个跳过的 1,4-二烯亚基，可通过钌催化的烯烃-炔烃偶联获得。之前的全合成表明报告的结构不正确；因此，为了将最大的灵活性纳入综合，最终目标是确定正确的结构，选择了高度收敛的方法。此外，自由使用催化不对称变换来设置单个立体中心。最终游戏设想了三种不同的策略，并且由于合成的高度收敛性，所有三种路线都与相同的三个关键中间体 5、6 和 7 断开连接。
• Structure Elucidation of (+)-Amphidinolide A by Total Synthesis and NMR Chemical Shift Analysis
  作者：Barry M. Trost、Paul E. Harrington

  DOI：10.1021/ja049292k

  日期：2004.4.28

  The structure elucidation of (+)-amphidinolide A, a cytotoxic macrolide, has been accomplished by employing a combination of NMR chemical shift analysis and total synthesis. Using the reported structure as a starting point, a number of diastereomers of amphidinolide A were prepared. The deviations of the chemical shifts of key protons in each isomer relative to the values reported for the isolated

  (+)-amphidinolide A（一种细胞毒性大环内酯）的结构解析是通过结合核磁共振化学位移分析和全合成完成的。使用报道的结构作为起点，制备了许多amphidinolide A的非对映异构体。每个异构体中关键质子的化学位移相对于分离材料的报告值的偏差用于确定相对立体化学中错误的位置。我们提出的 (+)-amphidinolide A 结构和分离材料的光谱数据非常一致。关键步骤，[Cp*Ru(MeCN)3]PF6 催化的烯烃-炔烃偶联，用于在合成的最后一步形成 20 元环。