(-)-(3S,4R,5S)-1-<(tert-butoxycarbonyl)amino>-3-(tert-butyldimethylsilyloxymethyl)-2-(ethoxycarbonyl)-4-phenyl-5-trimethylsilylpyrazolidine | 224572-35-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (-)-(3S,4R,5S)-1-<(tert-butoxycarbonyl)amino>-3-(tert-butyldimethylsilyloxymethyl)-2-(ethoxycarbonyl)-4-phenyl-5-trimethylsilylpyrazolidine
• CAS: 224572-35-4
• 化学式: C₂₇H₄₈N₂O₅Si₂
• 分子量: 536.86
• InChiKey: YMEUBQAJHLCRHH-ZLNRFVROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.03
• 重原子数：
  36.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  68.31
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (-)-(3S,4R,5S)-1-<(tert-butoxycarbonyl)amino>-3-(tert-butyldimethylsilyloxymethyl)-2-(ethoxycarbonyl)-4-phenyl-5-trimethylsilylpyrazolidine 在 氨 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以87%的产率得到(-)-(2S,3R,4S)-4-<(tert-butoxycarbonyl)amino>-O-(tert-butyldimethylsilyl)-2-<(ethoxycarbonyl)amino>-3-phenyl-4-trimethylsilyl-1-butanol
  参考文献：
  名称：

  First Highly Regio- and Diastereoselective [3+2] Cycloaddition of Chiral Nonracemic Alkenyl Fischer Carbene Complexes with Diazomethane Derivatives: Preparation and Synthetic Applications of Enantiomerically Pure Δ2-Pyrazolines

  摘要：

  The [3+2] cycloaddition of alkenyl Fischer carbene complexes 1 and 6 with diazomethane derivatives to give Delta(2)-pyrazoline carbenes 2, 4, and 7 is described. The conversion of (-)-8-phenylmenthol-derived carbenes 6 into pyrazoline esters 9 through a one-pot cycloaddition-protection-oxidation is presented as an expeditious route to enantiomerically pure 3-alkoxycarbon-yl-Delta(2)-pyrazolines in good yields and in a highly regio- and diastereoselective manner. Pyrazolidines 13 were synthesized in excellent overall yields from 9 through pyrazolines 11 and 12, the diastereoselective reduction of C=N bond being the key step. Azaprolines 16 and 17 were prepared in very good yields from epimeric trans-13 or cis-13 by oxidative deprotection of the silylated hydroxy group. In an alternative reaction, the pyrazolidine ring of 13 was reduced to obtain protected open-chain 2,4-diamino alcohols 19 with three chiral centers.

  DOI：

  10.1002/(sici)1521-3765(19990301)5:3<883::aid-chem883>3.0.co;2-0
• 作为产物：
  描述：

  在 咪唑 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 三乙基硼氢化锂 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 35.0h， 生成 (-)-(3S,4R,5S)-1-<(tert-butoxycarbonyl)amino>-3-(tert-butyldimethylsilyloxymethyl)-2-(ethoxycarbonyl)-4-phenyl-5-trimethylsilylpyrazolidine
  参考文献：
  名称：

  First Highly Regio- and Diastereoselective [3+2] Cycloaddition of Chiral Nonracemic Alkenyl Fischer Carbene Complexes with Diazomethane Derivatives: Preparation and Synthetic Applications of Enantiomerically Pure Δ2-Pyrazolines

  摘要：

  The [3+2] cycloaddition of alkenyl Fischer carbene complexes 1 and 6 with diazomethane derivatives to give Delta(2)-pyrazoline carbenes 2, 4, and 7 is described. The conversion of (-)-8-phenylmenthol-derived carbenes 6 into pyrazoline esters 9 through a one-pot cycloaddition-protection-oxidation is presented as an expeditious route to enantiomerically pure 3-alkoxycarbon-yl-Delta(2)-pyrazolines in good yields and in a highly regio- and diastereoselective manner. Pyrazolidines 13 were synthesized in excellent overall yields from 9 through pyrazolines 11 and 12, the diastereoselective reduction of C=N bond being the key step. Azaprolines 16 and 17 were prepared in very good yields from epimeric trans-13 or cis-13 by oxidative deprotection of the silylated hydroxy group. In an alternative reaction, the pyrazolidine ring of 13 was reduced to obtain protected open-chain 2,4-diamino alcohols 19 with three chiral centers.

  DOI：

  10.1002/(sici)1521-3765(19990301)5:3<883::aid-chem883>3.0.co;2-0