(2R,3R,5R)-2-((R)-3-Benzyloxy-2-methyl-propyl)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol | 799296-72-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,5R)-2-((R)-3-Benzyloxy-2-methyl-propyl)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol
• 英文别名: (2R,3R,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-[(2R)-2-methyl-3-phenylmethoxypropyl]oxolan-3-ol
• CAS: 799296-72-3
• 化学式: C₃₂H₄₂O₄Si
• 分子量: 518.769
• InChiKey: XSENWQKOYPWWLE-RSQMPJMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.32
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R,5R)-2-((R)-3-Benzyloxy-2-methyl-propyl)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol 在 palladium dihydroxide 咪唑 、 4-二甲氨基吡啶 、 草酰氯 、 氢气 、 二甲基亚砜 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 36.0h， 生成 (R)-3-[(2R,3R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-triethylsilanyloxy-tetrahydro-furan-2-yl]-2-methyl-propionaldehyde
  参考文献：
  名称：

  Synthesis of the Azaspiracid-1 Trioxadispiroketal

  摘要：

  The de novo analysis, design, and synthesis of the azaspiracid-1 trioxadispiroketal system is described. A revised structural model was developed on the basis of an independent analysis of the NMR spectral data of the natural product that fit all of the data and the thermodynamically favored spiroketal paradigm. This model was then tested via synthesis using a novel trioxadispiroketalization process and supported by spectroscopic correlation.

  DOI：

  10.1021/ol048581a
• 作为产物：
  描述：

  叔丁基二苯基氯硅烷 、 (2R,3R,5R)-2-((R)-3-Benzyloxy-2-methyl-propyl)-5-hydroxymethyl-tetrahydro-furan-3-ol 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以70%的产率得到(2R,3R,5R)-2-((R)-3-Benzyloxy-2-methyl-propyl)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol
  参考文献：
  名称：

  Synthesis of the Azaspiracid-1 Trioxadispiroketal

  摘要：

  The de novo analysis, design, and synthesis of the azaspiracid-1 trioxadispiroketal system is described. A revised structural model was developed on the basis of an independent analysis of the NMR spectral data of the natural product that fit all of the data and the thermodynamically favored spiroketal paradigm. This model was then tested via synthesis using a novel trioxadispiroketalization process and supported by spectroscopic correlation.

  DOI：

  10.1021/ol048581a

文献信息

• Synthesis of the Azaspiracid-1 Trioxadispiroketal
  作者：Lisa K. Geisler、Son Nguyen、Craig J. Forsyth

  DOI：10.1021/ol048581a

  日期：2004.11.1

  The de novo analysis, design, and synthesis of the azaspiracid-1 trioxadispiroketal system is described. A revised structural model was developed on the basis of an independent analysis of the NMR spectral data of the natural product that fit all of the data and the thermodynamically favored spiroketal paradigm. This model was then tested via synthesis using a novel trioxadispiroketalization process and supported by spectroscopic correlation.