{(1R,2S,3S)-3,4-Bis-benzyloxy-1-[(R)-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methoxy-methyl]-2-methoxy-butoxy}-tert-butyl-dimethyl-silane | 637020-43-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: {(1R,2S,3S)-3,4-Bis-benzyloxy-1-[(R)-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methoxy-methyl]-2-methoxy-butoxy}-tert-butyl-dimethyl-silane
• 英文别名: tert-butyl-[(1R,2R,3S,4S)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,3-dimethoxy-4,5-bis(phenylmethoxy)pentan-2-yl]oxy-dimethylsilane
• CAS: 637020-43-0
• 化学式: C₃₂H₅₀O₇Si
• 分子量: 574.83
• InChiKey: PRMMZFSWHKKXNH-WQOITCGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.36
• 重原子数：
  40
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  {(1R,2S,3S)-3,4-Bis-benzyloxy-1-[(R)-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methoxy-methyl]-2-methoxy-butoxy}-tert-butyl-dimethyl-silane 在 咪唑 、 4-甲基苯磺酸吡啶 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (2S,3R,4S,5R,6S)-6,7-Bis-benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethoxy-heptane-2,4-diol
  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：

  methoxy tetrafluoroborate 、 (1R,2R,3S,4S)-2-[tert-butyl(dimethyl)silyl]oxy-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4,5-bis(phenylmethoxy)pentane-1,3-diol 以78%的产率得到{(1R,2S,3S)-3,4-Bis-benzyloxy-1-[(R)-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methoxy-methyl]-2-methoxy-butoxy}-tert-butyl-dimethyl-silane
  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.