(1S,4R,5S,6S,7S)-2-benzyl-5,7-bis(tert-butyldimethylsilanyloxy)-6-triethylsilanyloxy-2-azabicyclo[2.2.2]octan-3-one | 676144-80-2

• 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)-2-benzyl-5,7-bis(tert-butyldimethylsilanyloxy)-6-triethylsilanyloxy-2-azabicyclo[2.2.2]octan-3-one
• 英文别名: (1S,4R,5S,6S,7S)-2-benzyl-5,7-bis[[tert-butyl(dimethyl)silyl]oxy]-6-triethylsilyloxy-2-azabicyclo[2.2.2]octan-3-one
• CAS: 676144-80-2
• 化学式: C₃₂H₅₉NO₄Si₃
• 分子量: 606.081
• InChiKey: PIEVIPAWPHQAPQ-QZLCNWOESA-N

物化性质

• 熔点：
  103-106 °C
• 沸点：
  580.7±50.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.59
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,4R,5S,6S,7S)-2-benzyl-5,7-bis(tert-butyldimethylsilanyloxy)-6-triethylsilanyloxy-2-azabicyclo[2.2.2]octan-3-one 在 盐酸 、 4-二甲氨基吡啶 、 lithium hydroxide 、 dimethyl sulfide borane 、 氨 、 sodium 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙腈 为溶剂， 反应 41.5h， 生成 (1S,2S,3S,4S,6S)-3-amino-6-hydroxymethylcyclohexane-1,2,4-triol
  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：

  (2S)-2,3-O-isopropylideneglyceraldehyde N-benzylimine 在 nickel dichloride 吡啶 、 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 草酰氯 、 叔丁基二甲硅基三氟甲磺酸酯 、 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 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 31.67h， 生成 (1S,4R,5S,6S,7S)-2-benzyl-5,7-bis(tert-butyldimethylsilanyloxy)-6-triethylsilanyloxy-2-azabicyclo[2.2.2]octan-3-one
  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

文献信息

• Variable Strategy toward Carbasugars and Relatives. 6.¹ Diastereoselective Synthesis of 2-Deoxy-2-amino-5a-carba-β-<scp>l</scp>-mannopyranuronic Acid and 2-Deoxy-2-amino-5a-carba-β-<scp>l</scp>-mannopyranose
  作者：Gloria Rassu、Luciana Auzzas、Vincenzo Zambrano、Paola Burreddu、Luigi Pinna、Lucia Battistini、Franca Zanardi、Giovanni Casiraghi

  DOI：10.1021/jo0357216

  日期：2004.3.1

  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.