(2S,3R,4S,5R)-5-[tert-butyl(dimethyl)silyl]oxy-2,4-dimethylheptane-1,3,4-triol | 933487-15-1

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2S,3R,4S,5R)-5-[tert-butyl(dimethyl)silyl]oxy-2,4-dimethylheptane-1,3,4-triol
• CAS: 933487-15-1
• 化学式: C₁₅H₃₄O₄Si
• 分子量: 306.518
• InChiKey: HGMDSVSUZAXVIO-KYEXWDHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5R)-5-[tert-butyl(dimethyl)silyl]oxy-2,4-dimethylheptane-1,3,4-triol 在 六甲基磷酰三胺 、 4-甲基苯磺酸吡啶 、 四丁基碘化铵 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 (2R,4R,5S)-4-[(1S,2R)-1-benzyloxy-2-tert-butyldimethylsiloxy-1-methylbutyl]-2-(p-methoxyphenyl)-5-methyl-1,3-dioxane
  参考文献：
  名称：

  Spirodiepoxide Reaction with Cuprates

  摘要：

  The first example of transition-metal-mediated transformations of spirodiepoxides and the first general method for carbon-carbon bond formation using the spirodiepoxide functional group are reported. Organocopper-mediated addition to spirodiepoxides gives direct access to densely functionalized hydroxy ketones. The process establishes two noncontiguous stereocenters and installs two oxygen atoms and a new carbon substituent. The utility of the methodology was demonstrated by preparing the stereotetrad of erythromycin in a short, efficient, and stereoselective route.

  DOI：

  10.1021/ja068813w
• 作为产物：
  描述：

  在 tetramethylammonium triacetoxyborohydride 作用下， 以 溶剂黄146 、 乙腈 为溶剂， 生成 (2S,3R,4S,5R)-5-[tert-butyl(dimethyl)silyl]oxy-2,4-dimethylheptane-1,3,4-triol
  参考文献：
  名称：

  Spirodiepoxide Reaction with Cuprates

  摘要：

  The first example of transition-metal-mediated transformations of spirodiepoxides and the first general method for carbon-carbon bond formation using the spirodiepoxide functional group are reported. Organocopper-mediated addition to spirodiepoxides gives direct access to densely functionalized hydroxy ketones. The process establishes two noncontiguous stereocenters and installs two oxygen atoms and a new carbon substituent. The utility of the methodology was demonstrated by preparing the stereotetrad of erythromycin in a short, efficient, and stereoselective route.

  DOI：

  10.1021/ja068813w