(2S,3S,5R)-5-[(E)-2-dimethoxyphosphorylethenyl]-2-pentyloxolan-3-ol | 1372769-27-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,5R)-5-[(E)-2-dimethoxyphosphorylethenyl]-2-pentyloxolan-3-ol
• CAS: 1372769-27-1
• 化学式: C₁₃H₂₅O₅P
• 分子量: 292.312
• InChiKey: RFBUILMTTUEIDT-DGWFCWONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3S,5R)-5-[(E)-2-dimethoxyphosphorylethenyl]-2-pentyloxolan-3-ol 在 sodium periodate 、 四氧化锇 、 N-甲基吗啉氧化物 、 柠檬酸 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 4.0h， 生成 (2R,4S,5S)-4-hydroxy-5-pentyltetrahydrofuran-2-carbaldehyde
  参考文献：
  名称：

  An Expeditious Total Synthesis of Both Diastereoisomeric Lipid Dihydroxytetrahydrofurans from Notheia anomala

  摘要：

  Short, high yielding syntheses of both diastereomers of the naturally occurring oxylipids 1 and 2 using a combination of organocatalytic hydroxylation of an aldehyde, alkene cross metathesis, and palladium(0) catalyzed cyclization chemistry (six-step process) are reported. Furthermore, the influence of the catalyst on the cross metathesis reaction of the homoallylic 1,2-diol has been studied in detail.

  DOI：

  10.1021/ol300597u
• 作为产物：
  描述：

  (4S,5S)-dec-1-ene-4,5-diol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 四(三苯基膦)钯 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 (2S,3S,5R)-5-[(E)-2-dimethoxyphosphorylethenyl]-2-pentyloxolan-3-ol
  参考文献：
  名称：

  An Expeditious Total Synthesis of Both Diastereoisomeric Lipid Dihydroxytetrahydrofurans from Notheia anomala

  摘要：

  Short, high yielding syntheses of both diastereomers of the naturally occurring oxylipids 1 and 2 using a combination of organocatalytic hydroxylation of an aldehyde, alkene cross metathesis, and palladium(0) catalyzed cyclization chemistry (six-step process) are reported. Furthermore, the influence of the catalyst on the cross metathesis reaction of the homoallylic 1,2-diol has been studied in detail.

  DOI：

  10.1021/ol300597u

文献信息

• An Expeditious Total Synthesis of Both Diastereoisomeric Lipid Dihydroxytetrahydrofurans from <i>Notheia anomala</i>
  作者：Sudeshna Roy、Christopher D. Spilling

  DOI：10.1021/ol300597u

  日期：2012.5.4

  Short, high yielding syntheses of both diastereomers of the naturally occurring oxylipids 1 and 2 using a combination of organocatalytic hydroxylation of an aldehyde, alkene cross metathesis, and palladium(0) catalyzed cyclization chemistry (six-step process) are reported. Furthermore, the influence of the catalyst on the cross metathesis reaction of the homoallylic 1,2-diol has been studied in detail.