tert-butyl-[(2R,3S,4R,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,5-bis(methoxymethoxy)-2-methylpentoxy]-diphenylsilane | 637020-22-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl-[(2R,3S,4R,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,5-bis(methoxymethoxy)-2-methylpentoxy]-diphenylsilane
• CAS: 637020-22-5
• 化学式: C₃₇H₆₂O₈Si₂
• 分子量: 691.065
• InChiKey: ZMKILQFCYCBMQC-DDAJPSLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.72
• 重原子数：
  47
• 可旋转键数：
  19
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl-[(2R,3S,4R,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,5-bis(methoxymethoxy)-2-methylpentoxy]-diphenylsilane 在 咪唑 、 四丁基氟化铵 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 生成 (4R,5R,6S)-4-[(1S,2R)-3-(tert-Butyl-diphenyl-silanyloxy)-1-methoxymethoxy-2-methyl-propyl]-6-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxymethoxy-2,2-dimethyl-[1,3]dioxane
  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 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 55.5h， 生成 tert-butyl-[(2R,3S,4R,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,5-bis(methoxymethoxy)-2-methylpentoxy]-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

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.