(2R,3S,4S,5R,6S)-3-((tert-butyldimethylsilyl)oxy)-5-nitro-6-phenyl-4-(thiophen-2-yl)-1-tosylpiperidin-2-ol | 1256489-31-2

• 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,4S,5R,6S)-3-((tert-butyldimethylsilyl)oxy)-5-nitro-6-phenyl-4-(thiophen-2-yl)-1-tosylpiperidin-2-ol
• 英文别名: (2R,3S,4S,5R,6S)-3-[tert-butyl(dimethyl)silyl]oxy-1-(4-methylphenyl)sulfonyl-5-nitro-6-phenyl-4-thiophen-2-ylpiperidin-2-ol
• CAS: 1256489-31-2
• 化学式: C₂₈H₃₆N₂O₆S₂Si
• 分子量: 588.821
• InChiKey: XXHBSOLCQHAXMK-UIPNDDLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.94
• 重原子数：
  39
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  149
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-[tert-butyl(dimethyl)silyl]oxy-4-nitro-3-thiophen-2-ylbutanal 、 N-亚苄基-4-甲基苯磺酰胺 在 溶剂黄146 、 四甲基胍 作用下， 以 二氯甲烷 为溶剂， 生成 (2R,3S,4S,5R,6S)-3-((tert-butyldimethylsilyl)oxy)-5-nitro-6-phenyl-4-(thiophen-2-yl)-1-tosylpiperidin-2-ol 、 (2R,3S,4S,5S,6S)-3-[tert-butyl(dimethyl)silyl]oxy-1-(4-methylphenyl)sulfonyl-5-nitro-6-phenyl-4-thiophen-2-ylpiperidin-2-ol
  参考文献：
  名称：

  One-Pot Enantioselective Syntheses of Iminosugar Derivatives Using Organocatalytic anti-Michael−anti-Aza-Henry Reactions

  摘要：

  Organocatalyst-controlled asymmetric anti-Michael reactions of (tert-butyldimethylsilyloxy)acetaidehyde with a range of nitroolefins, followed by an intermolecular aza-Henry reaction with imine, provided iminosugar derivatives with five contiguous stereocenters in very high enantiomeric excess in one pot. The stereochemistry of the aza-Henry reaction was substrate controlled and is explained by a six-membered cyclic transition-state model.

  DOI：

  10.1021/ol102292a

文献信息

• One-Pot Enantioselective Syntheses of Iminosugar Derivatives Using Organocatalytic <i>anti</i>-Michael−<i>anti</i>-Aza-Henry Reactions
  作者：Ritsuo Imashiro、Hisatoshi Uehara、Carlos F. Barbas

  DOI：10.1021/ol102292a

  日期：2010.11.19

  Organocatalyst-controlled asymmetric anti-Michael reactions of (tert-butyldimethylsilyloxy)acetaidehyde with a range of nitroolefins, followed by an intermolecular aza-Henry reaction with imine, provided iminosugar derivatives with five contiguous stereocenters in very high enantiomeric excess in one pot. The stereochemistry of the aza-Henry reaction was substrate controlled and is explained by a six-membered cyclic transition-state model.