(1S,4R,5S,6S,7S)-5,7-bis(tert-butyldimethylsilanyloxy)-3-oxo-6-triethylsilanyloxy-2-azabicyclo[2.2.2]octane-2-carboxylic acid tert-butyl ester | 676144-82-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (1S,4R,5S,6S,7S)-5,7-bis(tert-butyldimethylsilanyloxy)-3-oxo-6-triethylsilanyloxy-2-azabicyclo[2.2.2]octane-2-carboxylic acid tert-butyl ester
• CAS: 676144-82-4
• 化学式: C₃₀H₆₁NO₆Si₃
• 分子量: 616.074
• InChiKey: IJAJMBKJVMPRGQ-RYWAYVEBSA-N

物化性质

• 沸点：
  567.3±50.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.32
• 重原子数：
  40.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  74.3
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (1S,4R,5S,6S,7S)-5,7-bis(tert-butyldimethylsilanyloxy)-3-oxo-6-triethylsilanyloxy-2-azabicyclo[2.2.2]octane-2-carboxylic acid tert-butyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 以93%的产率得到(1R,2S,3S,4S,5S)-4-tert-butoxycarbonylamino-2,5-bis(tert-butyldimethylsilanyloxy)-3-triethylsilanyloxycyclohexanecarboxylic acid
  参考文献：
  名称：

  Variable Strategy toward Carbasugars and Relatives. 6.¹ Diastereoselective Synthesis of 2-Deoxy-2-amino-5a-carba-β-l-mannopyranuronic Acid and 2-Deoxy-2-amino-5a-carba-β-l-mannopyranose

  摘要：

  Efficient, total syntheses of novel 2-deoxy-2-amino-5a-carba-beta-L-mannopyranuronic acid (1) and 2-deoxy-2-amino-5a-carba-beta-L-mannopyranose (2), a positional stereoisomer of validamine, have been achieved in 28% and 24% overall yields and in 12 steps and 13 steps, respectively, from 2-[(tert-butyldimethylsilyl)oxy]furan (3) and (2S)-2,3-O-isopropylideneglyceraldehyde N-benzyl imine (4) via two highly diastereoselective Mukaiyama aldol-related chemical maneuvers. The strategy, which furnishes the targeted carbasugars in enantiopure forms, allows for complete control of the configuration at all five contiguous stereocenters of the targets by utilizing the sole element of chirality present in the aldimine progenitor 4.

  DOI：

  10.1021/jo0357216
• 作为产物：
  描述：

  (1'S,4''S,5S)-5-[benzylamino-(2,2-dimethyl-[1,3]dioxolan-4-yl)methyl]-4,5-dihydrofuran-2(3H)-one 在 吡啶 、 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 草酰氯 、 氨 、 sodium 、 溶剂黄146 、 二甲基亚砜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 34.5h， 生成 (1S,4R,5S,6S,7S)-5,7-bis(tert-butyldimethylsilanyloxy)-3-oxo-6-triethylsilanyloxy-2-azabicyclo[2.2.2]octane-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Variable Strategy toward Carbasugars and Relatives. 6.¹ Diastereoselective Synthesis of 2-Deoxy-2-amino-5a-carba-β-l-mannopyranuronic Acid and 2-Deoxy-2-amino-5a-carba-β-l-mannopyranose

  摘要：

  Efficient, total syntheses of novel 2-deoxy-2-amino-5a-carba-beta-L-mannopyranuronic acid (1) and 2-deoxy-2-amino-5a-carba-beta-L-mannopyranose (2), a positional stereoisomer of validamine, have been achieved in 28% and 24% overall yields and in 12 steps and 13 steps, respectively, from 2-[(tert-butyldimethylsilyl)oxy]furan (3) and (2S)-2,3-O-isopropylideneglyceraldehyde N-benzyl imine (4) via two highly diastereoselective Mukaiyama aldol-related chemical maneuvers. The strategy, which furnishes the targeted carbasugars in enantiopure forms, allows for complete control of the configuration at all five contiguous stereocenters of the targets by utilizing the sole element of chirality present in the aldimine progenitor 4.

  DOI：

  10.1021/jo0357216