2,3-O-(ethoxymethylene)-D-ribonic acid γ-lactone | 78508-93-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-O-(ethoxymethylene)-D-ribonic acid γ-lactone
• 英文别名: (3aR,6R,6aR)-2-ethoxy-6-(hydroxymethyl)-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-one
• CAS: 78508-93-7
• 化学式: C₈H₁₂O₆
• 分子量: 204.18
• InChiKey: BULIYJLVZZNMKE-CDRSNLLMSA-N

物化性质

• 沸点：
  380.0±42.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.99
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2,3-O-(ethoxymethylene)-D-ribonic acid γ-lactone 在 sodium hydroxide 、 溶剂黄146 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 6.0h， 生成 5-[4-[1-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-1-methylethyl]-thio-2,6-bis(1,1-dimethylethyl)phenoxy]-2(R),3(R),4(R)-trihydroxy-pentanoic acid
  参考文献：
  名称：

  Discovery of Novel Phenolic Antioxidants as Inhibitors of Vascular Cell Adhesion Molecule-1 Expression for Use in Chronic Inflammatory Diseases

  摘要：

  Vascular cell adhesion molecule-1 (VCAM-1) mediates recruitment of leukocytes to endothelial cells and is implicated in many inflammatory conditions. Since part of the signal transduction pathway that regulates the activation of VCAM-1 expression is redox-sensitive, compounds with antioxidant properties may have inhibitory effects on VCAM-1 expression. Novel phenolic compounds have been designed and synthesized starting from probucol (1). Many of these compounds demonstrated potent inhibitory effects on cytokine-induced VCAM-1 expression and displayed potent antioxidant effects in. vitro. Some of these derivatives (4o, 4p, 4w, and 4x) inhibited lipopolysaccharide (LPS)-induced secretion of pro-inflammatory cytokines such as tumor necrosis factor-alpha (TNF-alpha), interleukin-1beta (IL-1beta), and IL-6 from human peripheral blood mononuclear cells (hPBMCs) in a concentration-dependent manner in vitro and showed antiinflammatory effects in an animal model. Compounds 4ad and 4ae are currently in clinical trials for the treatment of rheumatoid arthritis (RA) and prevention of chronic organ transplant rejection, respectively.

  DOI：

  10.1021/jm049685u
• 作为产物：
  描述：

  D-(+)-核糖酸-1,4-内酯 生成 2,3-O-(ethoxymethylene)-D-ribonic acid γ-lactone
  参考文献：
  名称：

  OKABE, MASAMI;SUN, RUEN-CHU;TAM, STEVE Y. K.;TODARO-LOUIS, J.;COFFEN, DAV+, J. ORG. CHEM., 53,(1988) N 20, C. 4780-4786

  摘要：

  DOI：

文献信息

• Synthesis of the dideoxynucleosides "ddC" and "CNT" from glutamic acid, ribonolactone, and pyrimidine bases
  作者：Masami Okabe、Ruen Chu Sun、Steve Y. K. Tam、Louis J. Todaro、David L. Coffen

  DOI：10.1021/jo00255a021

  日期：1988.9
• Total synthesis of (+)-eldanolide from -ribonolactone
  作者：R.M. Ortuño、R. Mercé、J. Font

  DOI：10.1016/s0040-4039(00)84573-6

  日期：1986.1
• A short synthesis of ()-5-hydroxymethyl-(5)-furan-2-one and derivatives from -ribonolactone
  作者：P. Camps、J. Font、O. Ponsati

  DOI：10.1016/s0040-4039(01)90353-3

  日期：1981.1