(4S,5R)-N-tert-butoxycarbonyl-2,2-dimethyl-4-isobutyl-5-(1-trimethylsilylethynyl)oxazolidine | 254752-42-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S,5R)-N-tert-butoxycarbonyl-2,2-dimethyl-4-isobutyl-5-(1-trimethylsilylethynyl)oxazolidine
• CAS: 254752-42-6
• 化学式: C₁₉H₃₅NO₃Si
• 分子量: 353.577
• InChiKey: YRYDKMQGZNPWTJ-JKSUJKDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.65
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (4S,5R)-N-tert-butoxycarbonyl-2,2-dimethyl-4-isobutyl-5-(1-trimethylsilylethynyl)oxazolidine 在 ruthenium trichloride sodium periodate 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 反应 3.0h， 生成 (4S,5S)-N-tert-butoxycarbonyl-2,2-dimethyl-4-isobutyloxazolidine-5-carboxylic acid
  参考文献：
  名称：

  A Versatile Approach to N-Boc-statine and N-Boc-norstatine Based on the Reduction of 1-Trialkylsilyl Acetylenic Ketones. Strong Remote Effect of the C(1) Substituent on the Stereoselectivity

  摘要：

  [GRAPHICS]An efficient, unified approach to chiral, protected beta-hydroxy gamma-amino and alpha-hydroxy beta-amino acids derived from Boc-L-leucine has been accomplished on the basis of the oxazaborolidine-controlled, stereoselective reduction of 1-trialkylsilyl acetylenic ketones; stereoselectivity in the reduction step has shown strong dependence upon C(1) substitution.

  DOI：

  10.1021/ol991098t
• 作为产物：
  描述：

  2,2-二甲氧基丙烷 、 (3S,4S)-4-(tert-butoxycarbonylamino)-6-methyl-1-trimethylsilylhept-1-yn-3-ol 在 4-甲基苯磺酸吡啶 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 (4S,5S)-N-tert-butoxycarbonyl-2,2-dimethyl-4-isobutyl-5-(1-trimethylsilylethynyl)oxazolidine 、 (4S,5R)-N-tert-butoxycarbonyl-2,2-dimethyl-4-isobutyl-5-(1-trimethylsilylethynyl)oxazolidine
  参考文献：
  名称：

  A Versatile Approach to N-Boc-statine and N-Boc-norstatine Based on the Reduction of 1-Trialkylsilyl Acetylenic Ketones. Strong Remote Effect of the C(1) Substituent on the Stereoselectivity

  摘要：

  [GRAPHICS]An efficient, unified approach to chiral, protected beta-hydroxy gamma-amino and alpha-hydroxy beta-amino acids derived from Boc-L-leucine has been accomplished on the basis of the oxazaborolidine-controlled, stereoselective reduction of 1-trialkylsilyl acetylenic ketones; stereoselectivity in the reduction step has shown strong dependence upon C(1) substitution.

  DOI：

  10.1021/ol991098t