tert-butyl-[[(2R)-6-ethoxy-4-methoxy-3,6-dihydro-2H-pyran-2-yl]methoxy]-dimethylsilane | 1013918-19-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: tert-butyl-[[(2R)-6-ethoxy-4-methoxy-3,6-dihydro-2H-pyran-2-yl]methoxy]-dimethylsilane
• CAS: 1013918-19-8
• 化学式: C₁₅H₃₀O₄Si
• 分子量: 302.486
• InChiKey: XQBCFWOXUFQXLZ-KWCCSABGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.69
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl-[[(2R)-6-ethoxy-4-methoxy-3,6-dihydro-2H-pyran-2-yl]methoxy]-dimethylsilane 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以9.2 mg的产率得到(R)-6-((tert-butyldimethylsilyloxy)methyl)-4-methoxy-5,6-dihydro-2H-pyran-2-one
  参考文献：
  名称：

  Metathesis-based synthesis of 3-methoxy α,β-unsaturated lactones: total synthesis of (R)-kavain and of the C1–C6 fragment of jerangolid D

  摘要：

  The total synthesis of (R)-kavain and of the C1-C6 fragment of jerangolid D has been achieved in nine and seven steps, respectively, from commercially available dimethyl D-Malate. A metathesis reaction of vinyl ethers and a sulfoxide-modified Julia olefination have been employed as the key steps. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.12.113
• 作为产物：
  描述：

  tert-butyl-[(2R)-2-(1-ethoxyprop-2-enoxy)-4-methoxypent-4-enoxy]-dimethylsilane 在 Grubbs catalyst-2 作用下， 以 氘代苯 为溶剂， 反应 72.0h， 生成 tert-butyl-[[(2R)-6-ethoxy-4-methoxy-3,6-dihydro-2H-pyran-2-yl]methoxy]-dimethylsilane
  参考文献：
  名称：

  Metathesis-based synthesis of 3-methoxy α,β-unsaturated lactones: total synthesis of (R)-kavain and of the C1–C6 fragment of jerangolid D

  摘要：

  The total synthesis of (R)-kavain and of the C1-C6 fragment of jerangolid D has been achieved in nine and seven steps, respectively, from commercially available dimethyl D-Malate. A metathesis reaction of vinyl ethers and a sulfoxide-modified Julia olefination have been employed as the key steps. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.12.113

文献信息

• Metathesis-based synthesis of 3-methoxy α,β-unsaturated lactones: total synthesis of (R)-kavain and of the C1–C6 fragment of jerangolid D
  作者：Jiří Pospíšil、István E. Markó

  DOI：10.1016/j.tetlet.2007.12.113

  日期：2008.2

  The total synthesis of (R)-kavain and of the C1-C6 fragment of jerangolid D has been achieved in nine and seven steps, respectively, from commercially available dimethyl D-Malate. A metathesis reaction of vinyl ethers and a sulfoxide-modified Julia olefination have been employed as the key steps. (c) 2007 Elsevier Ltd. All rights reserved.