S-[2,4,6-tri(propan-2-yl)phenyl] (2R,3R,4S)-4-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-2,5-dimethylhexanethioate | 1247748-09-9

• 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: S-[2,4,6-tri(propan-2-yl)phenyl] (2R,3R,4S)-4-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-2,5-dimethylhexanethioate
• CAS: 1247748-09-9
• 化学式: C₂₉H₅₂O₃SSi
• 分子量: 508.882
• InChiKey: PYYHYPQTNMPMPM-QGDZQMKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.72
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  S-[2,4,6-tri(propan-2-yl)phenyl] (2R,3R,4S)-4-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-2,5-dimethylhexanethioate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成
  参考文献：
  名称：

  Direct Carbon−Carbon Bond Formation via Reductive Soft Enolization: A Kinetically Controlled syn-Aldol Addition of α-Halo Thioesters and Enolizable Aldehydes

  摘要：

  The direct addition of enolizable aldehydes and alpha-halo thioesters to produce beta-hydroxy thioesters enabled by reductive soft enolization is reported. The transformation is operationally simple and efficient and has the unusual feature of giving high syn-selectivity, which is the opposite of that produced for (thio)esters under conventional conditions. Moreover, excellent diastereoselectivity results when a chiral nonracemic alpha-hydroxy aldehyde derivative is used.

  DOI：

  10.1021/ja1057407
• 作为产物：
  描述：

  S-2,4,6-triisopropylphenyl α-iodothiopropionate 、 (S)-2-((tert-butyldimethylsilyl)oxy)-3-methylbutanal 在 三苯基膦 、 magnesium iodide 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到S-[2,4,6-tri(propan-2-yl)phenyl] (2R,3R,4S)-4-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-2,5-dimethylhexanethioate
  参考文献：
  名称：

  Direct Carbon−Carbon Bond Formation via Reductive Soft Enolization: A Kinetically Controlled syn-Aldol Addition of α-Halo Thioesters and Enolizable Aldehydes

  摘要：

  The direct addition of enolizable aldehydes and alpha-halo thioesters to produce beta-hydroxy thioesters enabled by reductive soft enolization is reported. The transformation is operationally simple and efficient and has the unusual feature of giving high syn-selectivity, which is the opposite of that produced for (thio)esters under conventional conditions. Moreover, excellent diastereoselectivity results when a chiral nonracemic alpha-hydroxy aldehyde derivative is used.

  DOI：

  10.1021/ja1057407

文献信息

• Direct Carbon−Carbon Bond Formation via Reductive Soft Enolization: A Kinetically Controlled <i>syn</i>-Aldol Addition of α-Halo Thioesters and Enolizable Aldehydes
  作者：Scott J. Sauer、Michelle R. Garnsey、Don M. Coltart

  DOI：10.1021/ja1057407

  日期：2010.10.13

  The direct addition of enolizable aldehydes and alpha-halo thioesters to produce beta-hydroxy thioesters enabled by reductive soft enolization is reported. The transformation is operationally simple and efficient and has the unusual feature of giving high syn-selectivity, which is the opposite of that produced for (thio)esters under conventional conditions. Moreover, excellent diastereoselectivity results when a chiral nonracemic alpha-hydroxy aldehyde derivative is used.