(4S,5R,6S)-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-[(1S)-1-hydroxyethyl]-2,2-dimethyl-1,3-dioxan-5-ol | 637020-33-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,5R,6S)-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-[(1S)-1-hydroxyethyl]-2,2-dimethyl-1,3-dioxan-5-ol
• CAS: 637020-33-8
• 化学式: C₁₃H₂₄O₆
• 分子量: 276.33
• InChiKey: JMXSKZPEXZIYNZ-QUARPLMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N'-羰基二咪唑 、 (4S,5R,6S)-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-[(1S)-1-hydroxyethyl]-2,2-dimethyl-1,3-dioxan-5-ol 以91%的产率得到(4S,4aS,8R,8aR)-8-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4,6,6-trimethyl-tetrahydro-[1,3]dioxino[5,4-d][1,3]dioxin-2-one
  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 palladium dihydroxide 氯代二环己基硼烷 、 四丁基氟化铵 、 氢气 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 丙酮 为溶剂， 反应 7.5h， 生成 (4S,5R,6S)-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-[(1S)-1-hydroxyethyl]-2,2-dimethyl-1,3-dioxan-5-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

文献信息

• Double Diastereoselection in Aldol Reactions Mediated by Dicyclohexylchloroborane between <scp>l</scp>-Erythrulose Derivatives and Chiral Aldehydes. The Felkin−Anh versus Cornforth Dichotomy
  作者：J. Alberto Marco、Miguel Carda、Santiago Díaz-Oltra、Juan Murga、Eva Falomir、Harald Roeper

  DOI：10.1021/jo035159j

  日期：2003.10.1

  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.