(2R*,3S*)-1-acetoxy-3-(N-benzylacetamido)-2-(dimethylphenylsilyl)-3-phenylpropane | 146060-99-3

• 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: (2R*,3S*)-1-acetoxy-3-(N-benzylacetamido)-2-(dimethylphenylsilyl)-3-phenylpropane
• 英文别名: [(2R,3S)-3-[acetyl(benzyl)amino]-2-[dimethyl(phenyl)silyl]-3-phenylpropyl] acetate
• CAS: 146060-99-3
• 化学式: C₂₈H₃₃NO₃Si
• 分子量: 459.66
• InChiKey: KWDMSHSFWDWTJD-NSOVKSMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.33
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R*,3S*)-1-acetoxy-3-(N-benzylacetamido)-2-(dimethylphenylsilyl)-3-phenylpropane 在 potassium fluoride 、 双氧水 、 溴 、 potassium hydrogencarbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 生成 Acetic acid (2R,3S)-3-(acetyl-benzyl-amino)-2-hydroxy-3-phenyl-propyl ester
  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：

  methyl (2R*,3S*)-3-benzylamino-2-(dimethylphenylsilyl)-3-phenylpropionate 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.67h， 生成 (2R*,3S*)-1-acetoxy-3-(N-benzylacetamido)-2-(dimethylphenylsilyl)-3-phenylpropane
  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