tert-butyl-[(2S)-2-[(4S,5R,6R)-5-[tert-butyl(dimethyl)silyl]oxy-6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxan-4-yl]propoxy]-diphenylsilane | 637020-17-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl-[(2S)-2-[(4S,5R,6R)-5-[tert-butyl(dimethyl)silyl]oxy-6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxan-4-yl]propoxy]-diphenylsilane
• CAS: 637020-17-8
• 化学式: C₃₆H₅₈O₆Si₂
• 分子量: 643.024
• InChiKey: LROIHFLYMHNQAT-NBUBIBOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.26
• 重原子数：
  44
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl-[(2S)-2-[(4S,5R,6R)-5-[tert-butyl(dimethyl)silyl]oxy-6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxan-4-yl]propoxy]-diphenylsilane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到(2S)-2-[(4S,5R,6R)-5-[tert-butyl(dimethyl)silyl]oxy-6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxan-4-yl]propan-1-ol
  参考文献：
  名称：

  Double Diastereoselection in Aldol Reactions Mediated by Dicyclohexylchloroborane between l-Erythrulose Derivatives and Chiral Aldehydes. The Felkin−Anh versus Cornforth Dichotomy

  摘要：

  Both matched and mismatched diastereoselections have been observed in aldol reactions of the B,B-dicyclohexylboron enolate of a protected L-erythrulose derivative with a range of chiral aldehydes. The stereochemical outcome of reactions with alpha-methyl aldehydes can be adequately explained within the Felkin-Anh paradigm. In the case of alpha-oxygenated aldehydes, however, strict adherence to this model does not allow for a satisfactory account of the observed results. In such cases, the Cornforth model provides a much better explanation.

  DOI：

  10.1021/jo035159j
• 作为产物：
  描述：

  2-[tert-butyl(dimethyl)silyl]oxy-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanone 在 氯代二环己基硼烷 、 对甲苯磺酸 、 三乙胺 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 7.5h， 生成 tert-butyl-[(2S)-2-[(4S,5R,6R)-5-[tert-butyl(dimethyl)silyl]oxy-6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxan-4-yl]propoxy]-diphenylsilane
  参考文献：
  名称：

  Double Diastereoselection in Aldol Reactions Mediated by Dicyclohexylchloroborane between l-Erythrulose Derivatives and Chiral Aldehydes. The Felkin−Anh versus Cornforth Dichotomy

  摘要：

  Both matched and mismatched diastereoselections have been observed in aldol reactions of the B,B-dicyclohexylboron enolate of a protected L-erythrulose derivative with a range of chiral aldehydes. The stereochemical outcome of reactions with alpha-methyl aldehydes can be adequately explained within the Felkin-Anh paradigm. In the case of alpha-oxygenated aldehydes, however, strict adherence to this model does not allow for a satisfactory account of the observed results. In such cases, the Cornforth model provides a much better explanation.

  DOI：

  10.1021/jo035159j