(3R,4S,5R)-3,4-Bis<(tert-butyldimethylsilyl)oxy>-5-(2-hydroxyethyl)-1-benzyl-2-pyrrolinone | 163002-05-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (3R,4S,5R)-3,4-Bis<(tert-butyldimethylsilyl)oxy>-5-(2-hydroxyethyl)-1-benzyl-2-pyrrolinone
• 英文别名: (3R*,4S*,5R*)-1-benzyl-3,4-bis(tert-butyldimethylsilyloxy)-5-(2-hydroxyethyl)-2-pyrrolidinone；(3R,4S,5R)-1-benzyl-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-(2-hydroxyethyl)pyrrolidin-2-one
• CAS: 163002-05-9
• 化学式: C₂₅H₄₅NO₄Si₂
• 分子量: 479.808
• InChiKey: GNNLISPZTMTXCR-BHIFYINESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.56
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,4S,5R)-3,4-Bis<(tert-butyldimethylsilyl)oxy>-5-(2-hydroxyethyl)-1-benzyl-2-pyrrolinone 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 2-[(2R,3S,4S)-1-Benzyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-pyrrolidin-2-yl]-ethanol
  参考文献：
  名称：

  A Practical and Divergent Way to Trihydroxylated Pyrrolidine Derivatives as Potential Glycosidase Inhibitors via Stereoselective Intermolecular cis-Amidoalkylations

  摘要：

  A practical and divergent way from the common tartrimide 1 to trihydroxylated pyrrolidines 2a-h as potential glycosidase inhibitors has been developed. cis-Amidoalkylations on the acyliminium intermediate 5 of the corresponding TBS-protected tartaric imide with the tin reagents afforded the desired structures 6a-c in good yields and high selectivities. In this reaction the adjacent OTBS group controls the stereoselectivity in the presence of a Lewis acid MgBr2. Transformations to each desired pyrrolidine could be achieved via efficient methods including selective protection, functionalization of the unsaturated bonds, and reduction of the amide group.

  DOI：

  10.1021/jo00106a021
• 作为产物：
  描述：

  [(2R,3S,4R)-1-Benzyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-oxo-pyrrolidin-2-yl]-acetaldehyde 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (3R,4S,5R)-3,4-Bis<(tert-butyldimethylsilyl)oxy>-5-(2-hydroxyethyl)-1-benzyl-2-pyrrolinone
  参考文献：
  名称：

  A Practical and Divergent Way to Trihydroxylated Pyrrolidine Derivatives as Potential Glycosidase Inhibitors via Stereoselective Intermolecular cis-Amidoalkylations

  摘要：

  A practical and divergent way from the common tartrimide 1 to trihydroxylated pyrrolidines 2a-h as potential glycosidase inhibitors has been developed. cis-Amidoalkylations on the acyliminium intermediate 5 of the corresponding TBS-protected tartaric imide with the tin reagents afforded the desired structures 6a-c in good yields and high selectivities. In this reaction the adjacent OTBS group controls the stereoselectivity in the presence of a Lewis acid MgBr2. Transformations to each desired pyrrolidine could be achieved via efficient methods including selective protection, functionalization of the unsaturated bonds, and reduction of the amide group.

  DOI：

  10.1021/jo00106a021

文献信息

• Pyridonecarboxylic acid derivatives and intermediates for the synthesis
  申请人：Dainippon Pharmaceutical Co., Ltd.

  公开号：US06017911A1

  公开（公告）日：2000-01-25

  This invention relates to pyridonecarboxylic acid derivatives of the following general formula, esters thereof and salts thereof, as well as pharmaceutical preparations containing them. ##STR1## wherein: R is cycloalkyl which may be substituted by halogen, or the like; X is hydrogen, lower alkyl, amino or the like; Y is hydrogen or halogen; A is nitrogen or a group of the formula C--Z in which Z is lower alkoxy that may be substituted by halogen, or the like; R.sub.1 and R.sub.2 may be the same or different and are each hydrogen or the like; R.sub.3 is hydrogen or lower alkyl; R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8 and R.sub.9 may be the same or different and are each hydrogen, halogen or lower alkyl; m is 0 or 1; and n and p may be the same or different and are each 0 or 1. This invention also relates to bicyclic amine compounds useful as direct intermediates for the synthesis of the above-described pyridonecarboxylic acid derivatives.

  本发明涉及以下一般式、其酯和盐的吡啶酮羧酸衍生物，以及含有它们的制药制剂。其中：R是环烷基，可以被卤素等取代；X是氢，低碳基，氨基或类似物；Y是氢或卤素；A是氮或C-Z式的基团，其中Z是可以被卤素等取代的低烷氧基；R1和R2可以相同也可以不同，分别是氢或类似物；R3是氢或低碳基；R4、R5、R6、R7、R8和R9可以相同也可以不同，分别是氢、卤素或低碳基；m为0或1；n和p可以相同也可以不同，分别为0或1。本发明还涉及用作合成上述吡啶酮羧酸衍生物的直接中间体的双环胺化合物。