(2R,3S)-2-[(2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-pyrrolidin-2-yl]-3-(tert-butyl-diphenyl-silanyloxy)-thiobutyric acid S-propyl ester | 230646-79-4

• 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: (2R,3S)-2-[(2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-pyrrolidin-2-yl]-3-(tert-butyl-diphenyl-silanyloxy)-thiobutyric acid S-propyl ester
• CAS: 230646-79-4
• 化学式: C₃₃H₅₃NO₃SSi₂
• 分子量: 600.026
• InChiKey: NKERHGBCWSYWNB-ZDIDPRFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.99
• 重原子数：
  40.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  47.56
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2R,3S)-2-[(2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-pyrrolidin-2-yl]-3-(tert-butyl-diphenyl-silanyloxy)-thiobutyric acid S-propyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以70%的产率得到(2R,3S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-((2S,4R)-4-hydroxy-pyrrolidin-2-yl)-thiobutyric acid S-propyl ester
  参考文献：
  名称：

  Kinetic Resolution of Diiron Acyl Complexes—An Approach to Asymmetric Bicyclic -Lactams

  摘要：

  Kinetic resolution is achieved in the reaction of racemic diiron complexes like 1 with the chiral nitrone (-)-2. Oxidative removal of the metal and reductive cleavage of the N-O bond provides β-amino acids. This sequence was used in the synthesis of β-amino acids as well as the corresponding β-lactams 4 (via 3).

  DOI：

  10.1002/(sici)1521-3773(19990419)38:8<1116::aid-anie1116>3.0.co;2-m
• 作为产物：
  描述：

  (4R)-4-(t-butyldimethylsilyloxy)-1-pyrroline N-oxide 在 咪唑 、 水 、 溶剂黄146 、 锌 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 (2R,3S)-2-[(2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-pyrrolidin-2-yl]-3-(tert-butyl-diphenyl-silanyloxy)-thiobutyric acid S-propyl ester
  参考文献：
  名称：

  Kinetic Resolution of Diiron Acyl Complexes—An Approach to Asymmetric Bicyclic -Lactams

  摘要：

  Kinetic resolution is achieved in the reaction of racemic diiron complexes like 1 with the chiral nitrone (-)-2. Oxidative removal of the metal and reductive cleavage of the N-O bond provides β-amino acids. This sequence was used in the synthesis of β-amino acids as well as the corresponding β-lactams 4 (via 3).

  DOI：

  10.1002/(sici)1521-3773(19990419)38:8<1116::aid-anie1116>3.0.co;2-m