methyl (E,5S,6R)-5,6,7-trihydroxyhept-2-enoate | 78606-78-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (E,5S,6R)-5,6,7-trihydroxyhept-2-enoate
• CAS: 78606-78-7
• 化学式: C₈H₁₄O₅
• 分子量: 190.196
• InChiKey: XMFYPKRSVDOUAV-QTLAMRMRSA-N

物化性质

• 沸点：
  382.1±42.0 °C(Predicted)
• 密度：
  1.259±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.18
• 重原子数：
  13.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  86.99
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl (E,5S,6R)-5,6,7-trihydroxyhept-2-enoate 在 咪唑 、 palladium on activated charcoal 、 水 、 氢气 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.5h， 生成 (5S,6R)-Methyl 5,6-di(tert-butyldimethylsiloxy)-7-hydroxyheptanoate
  参考文献：
  名称：

  Synthesis of Bifunctional Lipoxin‐Derived Enzyme‐Triggered CO‐Releasing Molecules (LipET‐CORMs)

  摘要：

  AbstractIn an attempt to develop new anti‐inflammatory agents which act by co‐release of carbon monoxide (CO) and a specialized pro‐resolving mediator, we designed conjugates of a lipoxin A4 analogue and an acyloxycyclohexadiene‐Fe(CO)3 complex as an esterase‐triggered CO‐releasing molecule (ET‐CORM). After adjustment of the protecting group strategy, two of such compounds were successfully prepared by total synthesis (12 steps; 4–5 % overall yield) starting from deoxy‐d‐ribose and exploiting a Wittig olefination and an intermolecular Heck reaction as key C−C bond‐forming steps. A crucial late reduction of an aryl‐ketone moiety in the presence of a highly sensitive dienol ester functionality was achieved with BH3‐SMe2 in the presence of catalytic amounts of NaBH4. Both target compounds were dose‐dependently toxic towards cultured human umbilical vein endothelial cells (HUVEC), with LipET‐CORM 1‐A being slightly more toxic. While induction of heme oxygenase 1 (HO‐1) in HUVEC was observed for both compounds, they did not inhibit TNF‐α‐mediated VCAM‐1 expression in these cells. In M2 polarized macrophages HO‐1 expression was more pronounced as compared to M1 polarized macrophages. In both types of macrophages HO‐1 expression was downregulated by lipopolysaccharide, but only in M2 macrophages HO‐1 expression was rescued by LipET‐CORM. 15‐Lipoxygenase (15‐LO) was only expressed in M2 macrophages and was not influenced by LipET‐CORM. Collectively our data demonstrate that LipET‐CORMs induce HO‐1 expression in endothelial cells and M2 polarized macrophages. The role of the intra‐cellular released lipoxin A4 in resolution of inflammation, however, remains to be assessed.

  DOI：

  10.1002/ejoc.202201424
• 作为产物：
  描述：

  (2R,3S)-5,5-bis(ethylthio)pentane-1,2,3-triol 在 N-溴代丁二酰亚胺(NBS) 、 水 作用下， 以 乙腈 为溶剂， 生成 methyl (E,5S,6R)-5,6,7-trihydroxyhept-2-enoate
  参考文献：
  名称：

  1 H NMR方法，用于确定1,2,3-prim，sec，sec-triols的绝对构型。

  摘要：

  可以通过比较tris-（R）-和tris-（S）-MPA酯衍生物的1H NMR光谱来确定1,2,3-prim，sec，sec-三醇的绝对构型。用24个已知绝对配置的三醇和一个使用两个参数Deltadelta（RS）（H3）的协议以及Deltadelta RS（H2）和Deltadelta RS（H3）之间的差=绝对值（Delta（Deltadelta RS ））-介绍了其在确定其他三醇的绝对构型中的应用。

  DOI：

  10.1021/ol0616135

文献信息

• Convergent Synthesis of <i>trans</i>-Fused Oxane Ring Systems Based on Ni^II/Cr^II-Mediated Cross-coupling Reactions
  作者：M. Teresa Díaz、Ruby L. Pérez、Elsa Rodríguez、José L. Ravelo、Julio D. Martín

  DOI：10.1055/s-2001-11398

  日期：——

  A general method for the convergent assembly of polyether structures has been developed based on a NiII/CrII-mediated cross-coupling reaction of alkenyl iodides with aldehydes. The present method allowed coupling to oxane rings via acetal cyclization and reductive etherification reactions.

  基于 NiII/CrII 介导的烯基碘化物与醛的交叉偶联反应，开发了一种聚合聚醚结构的通用方法。本方法允许通过缩醛环化和还原醚化反应与恶烷环偶联。
• A Stereocontrolled and effective synthesis of leukotriene B (1).
  作者：E.J. Corey、Anthony Marfat、John Munroe、Kwan Soo Kim、Paul B. Hopkins、Francis Brion

  DOI：10.1016/s0040-4039(01)90241-2

  日期：——

  An efficient synthesis of leukotriene B (1) is reported which renders this important substance accessible in quantity. The process is convergent and includes a novel method for stereospecific generation of the conjugated triene unit.

  据报道，白三烯B（1）的有效合成使得该重要物质在数量上可及。该过程是收敛的，并且包括用于共轭三烯单元的立体有规生成的新方法。
• Synthetic studies towards ciguatoxin via acetal/γ-oxovinyl stannane condensation: A convergent approach
  作者：JoséLuis Ravelo、Alicia Regueiro、Elsa Rodríguez、José de Vera、Julio D. Martín

  DOI：10.1016/0040-4039(96)00409-1

  日期：1996.4

  A two-directional approach converting acetals to O-linked oxacycles, by way of intramolecular allyl tin-acetal condensation, is described.

  描述了通过分子内烯丙基锡-缩醛缩合将缩醛转化为O-连接的氧杂环的双向方法。
• The Stereochemistry of 1,2,3-Triols Revealed by¹H NMR Spectroscopy: Principles and Applications
  作者：Félix Freire、Enrique Lallana、Emilio Quiñoá、Ricardo Riguera

  DOI：10.1002/chem.200901505

  日期：2009.11.9

  The conformational compositions of the tris(α‐methoxy‐α‐phenylacetic acid) ester derivatives of 1,2,3‐prim,sec,sec‐triols are presented. These conformations have been determined by theoretical and experimental data (i.e., energy‐ and chemical‐shift calculations, circular dichroism (CD) experiments, coupling‐constant analysis, enantioselective deuteration experiments, and low‐temperature NMR spectroscopic

  介绍了1,2,3- prim，sec，sec- triols的三（α-甲氧基-α-苯基乙酸）酯衍生物的构象组成。这些构象已由理论和实验数据确定（例如，能量和化学位移计算，圆二色性（CD）实验，耦合常数分析，对映选择性氘化实验和低温NMR光谱研究）。由于在最显著构象异构体的各向异性的影响的详细分析1 1 H NMR谱所支持的之间的相关性1 1 H NMR谱（Δ δ RS的H（3'）和值|Δ（Δ δ RS）| 参数）和基板的绝对配置。该研究还允许根据邻偶合常数和相对化学位移来鉴定Pro - R和Pro-S亚甲基质子。
• Nicolaou; Wallace, Paul A.; Shi, Shuhao, Chemistry - A European Journal, 1999, vol. 5, # 2, p. 618 - 627
  作者：Nicolaou、Wallace, Paul A.、Shi, Shuhao、Ouellette, Michael A.、Bunnage, Mark E.、Gunzner, Janet L.、Agrios, Konstantinos A.、Shi, Guo-Qiang、Gaertner, Peter、Yang, Zhen

  DOI：——

  日期：——