cyclohexyl (2R*,3S*)-2-(tert-butyldimethylsilyl)-3-hydroxy-5-phenylpentanoate | 138964-27-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: cyclohexyl (2R*,3S*)-2-(tert-butyldimethylsilyl)-3-hydroxy-5-phenylpentanoate
• 英文别名: cyclohexyl (2R,3S)-2-[tert-butyl(dimethyl)silyl]-3-hydroxy-5-phenylpentanoate
• CAS: 138964-27-9
• 化学式: C₂₃H₃₈O₃Si
• 分子量: 390.638
• InChiKey: LIMJMJSJZVDIMM-LEWJYISDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.73
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cyclohexyl (2R*,3S*)-2-(tert-butyldimethylsilyl)-3-hydroxy-5-phenylpentanoate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 生成 cyclohexyl (Z)-5-phenylpent-2-enoate 、 cyclohexyl (E)-5-phenylpent-2-enoate
  参考文献：
  名称：

  Chemistry of silylketenes: a simple preparation of α-silyl-α-stannylacetic esters and their stereoselective Reformatsky-type reaction with aldehydes or aldimines

  摘要：

  Silylketenes 1a, b reacted smoothly with alkoxystannanes 3 to give the corresponding alpha-silyl-alpha-stannylacetates 4 almost quantitatively. Treatment of 4 with TiCl4 caused selective cleavage of the C-Sn bond to bring about Reformatsky-type reaction with aldehydes 6 giving beta-hydroxy-alpha-silyl esters 7. These two steps were carried out by one-pot operation, and variously substituted compounds 7 were obtained with high syn-selectivity (52-> 96% d.e.) in 41-89% yields. A similar one-pot procedure starting from la-c, 3, and aldimines 11 also provided the corresponding beta-amino-alpha-silyl esters 12 with excellent syn-selectivity (greater-than-or-equal-to 96% d.e.) in 64-94% yields. Stereocontrolled preparation of both (E)- and (Z)-alpha,beta-unsaturated esters 8 and a syn-amino diol derivative 17 from syn-7 and syn-12, respectively, is also described.

  DOI：

  10.1039/p19920002813
• 作为产物：
  描述：

  苯丙醛 、 tert-butyldimethylsilylketene 、 Cyclohexyloxy-tributyl-stannan 在 四氯化钛 、 zinc(II) iodide 作用下， 生成 cyclohexyl (2R*,3S*)-2-(tert-butyldimethylsilyl)-3-hydroxy-5-phenylpentanoate
  参考文献：
  名称：

  Chemistry of silylketenes: a simple preparation of α-silyl-α-stannylacetic esters and their stereoselective Reformatsky-type reaction with aldehydes or aldimines

  摘要：

  Silylketenes 1a, b reacted smoothly with alkoxystannanes 3 to give the corresponding alpha-silyl-alpha-stannylacetates 4 almost quantitatively. Treatment of 4 with TiCl4 caused selective cleavage of the C-Sn bond to bring about Reformatsky-type reaction with aldehydes 6 giving beta-hydroxy-alpha-silyl esters 7. These two steps were carried out by one-pot operation, and variously substituted compounds 7 were obtained with high syn-selectivity (52-> 96% d.e.) in 41-89% yields. A similar one-pot procedure starting from la-c, 3, and aldimines 11 also provided the corresponding beta-amino-alpha-silyl esters 12 with excellent syn-selectivity (greater-than-or-equal-to 96% d.e.) in 64-94% yields. Stereocontrolled preparation of both (E)- and (Z)-alpha,beta-unsaturated esters 8 and a syn-amino diol derivative 17 from syn-7 and syn-12, respectively, is also described.

  DOI：

  10.1039/p19920002813

文献信息

• Chemistry of silylketenes: a simple preparation of α-silyl-α-stannylacetic esters and their stereoselective Reformatsky-type reaction with aldehydes or aldimines
  作者：Shuji Akai、Yasunori Tsuzuki、Satoshi Matsuda、Shinji Kitagaki、Yasuyuki Kita

  DOI：10.1039/p19920002813

  日期：——

  Silylketenes 1a, b reacted smoothly with alkoxystannanes 3 to give the corresponding alpha-silyl-alpha-stannylacetates 4 almost quantitatively. Treatment of 4 with TiCl4 caused selective cleavage of the C-Sn bond to bring about Reformatsky-type reaction with aldehydes 6 giving beta-hydroxy-alpha-silyl esters 7. These two steps were carried out by one-pot operation, and variously substituted compounds 7 were obtained with high syn-selectivity (52-> 96% d.e.) in 41-89% yields. A similar one-pot procedure starting from la-c, 3, and aldimines 11 also provided the corresponding beta-amino-alpha-silyl esters 12 with excellent syn-selectivity (greater-than-or-equal-to 96% d.e.) in 64-94% yields. Stereocontrolled preparation of both (E)- and (Z)-alpha,beta-unsaturated esters 8 and a syn-amino diol derivative 17 from syn-7 and syn-12, respectively, is also described.