methyl-1-(tert-butyldimethylsilyloxy)-2-methyl-4-butenoate | 98540-07-9

• 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-1-(tert-butyldimethylsilyloxy)-2-methyl-4-butenoate
• 英文别名: methyl 4-[tert-butyl(dimethyl)silyl]oxy-3-methylbut-2-enoate
• CAS: 98540-07-9
• 化学式: C₁₂H₂₄O₃Si
• 分子量: 244.406
• InChiKey: HTJIGOGNVJJPBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.13
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl-1-(tert-butyldimethylsilyloxy)-2-methyl-4-butenoate 在 锂硼氢 、 甲基磺酰胺 、 AD-mix β 、 camphor-10-sulfonic acid 、 碳酸氢钠 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 2.0h， 生成 (4R,5S)-5-[(tert-butyldimethylsilanyloxymethyl)-2-methoxy-5-methyl[1,3]dio-xolan-4-yl]methanol
  参考文献：
  名称：

  Synthesis of Methylerythritol Phosphate Analogues and Their Evaluation as Alternate Substrates for IspDF and IspE from Agrobacterium tumefaciens

  摘要：

  The methylerythritol phosphate biosynthetic pathway, found in most Bacteria, some parasitic protists, and plant chloroplasts, converts D-glyceraldehyde phosphate and pyruvate to isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP), where it intersects with the mevalonate pathway found in some Bacteria, Archaea, and Eukarya, including the cytosol of plants. D-3-Methylerythritol-4-phosphate (MEP), the first pathway-specific intermediate in the pathway, is converted to IPP and DMAPP by the consecutive action of the IspD-H proteins. We synthesized five D-MEP analogues-D-erythritol-4-phosphate (EP), D-3-methylthrietol-4-phosphate (MTP), D-3-ethylerythritol-4-phosphate (EEP), D-1-amino-3-methylerythritol-4-phosphate (NMEP), and D-3-methylerythritol-4-thiolophosphate (MESP)-and studied their ability to function as alternative substrates for the reactions catalyzed by the IspDF fusion and IspE proteins from Agrobacterium tumefaciens, which covert MEP to the corresponding eight-membered cyclic diphosphate. All of the analogues, except MTP, and their products were substrates for the three consecutive enzymes.

  DOI：

  10.1021/jo501529k

文献信息

• Direct approach to the bakkanes: A synthesis of (±)-homogynolide-B
  作者：Fernando Coelho、Jean-Pierre Deprés、Timothy J. Brocksom、Andrew E. Greene

  DOI：10.1016/s0040-4039(00)95255-9

  日期：——